Carbon nanomaterials: multi-functional agents for biomedical fluorescence and Raman imaging.

Carbon based nanomaterials have emerged over the last few years as important agents for biomedical fluorescence and Raman imaging applications. These spectroscopic techniques utilize either fluorescently labelled carbon nanomaterials or the intrinsic photophysical properties of the carbon nanomaterial. In this review article we present the utilization and performance of several classes of carbon nanomaterials, namely carbon nanotubes, carbon nanohorns, carbon nanoonions, nanodiamonds and different graphene derivatives, which are currently employed for in vitro as well as in vivo imaging in biology and medicine. A variety of different approaches, imaging agents and techniques are examined and the specific properties of the various carbon based imaging agents are discussed. Some theranostic carbon nanomaterials, which combine diagnostic features (i.e. imaging) with cell specific targeting and therapeutic approaches (i.e. drug delivery or photothermal therapy), are also included in this overview.

[1]  E. Parisini,et al.  Boron dipyrromethene (BODIPY) functionalized carbon nano-onions for high resolution cellular imaging. , 2014, Nanoscale.

[2]  Xungai Wang,et al.  Graphene oxide nanoparticles as a nonbleaching optical probe for two-photon luminescence imaging and cell therapy. , 2012, Angewandte Chemie.

[3]  R. Jasti,et al.  Gram-scale synthesis and crystal structures of [8]- and [10]CPP, and the solid-state structure of C60@[10]CPP , 2012 .

[4]  Valeria Nicolosi,et al.  Ordered DNA wrapping switches on luminescence in single-walled nanotube dispersions. , 2008, Journal of the American Chemical Society.

[5]  A. Atala,et al.  Carbon nanotube applications for tissue engineering. , 2007, Biomaterials.

[6]  Andre K. Geim,et al.  The rise of graphene. , 2007, Nature materials.

[7]  Hui Jiang,et al.  Gold nanoclusters and graphene nanocomposites for drug delivery and imaging of cancer cells. , 2011, Angewandte Chemie.

[8]  K Kostarelos,et al.  Promises, facts and challenges for carbon nanotubes in imaging and therapeutics. , 2009, Nature nanotechnology.

[9]  Q. Tu,et al.  Diagnostic applications of Raman spectroscopy. , 2012, Nanomedicine : nanotechnology, biology, and medicine.

[10]  S. Gambhir,et al.  Quantum Dots for Live Cells, in Vivo Imaging, and Diagnostics , 2005, Science.

[11]  H. Dai,et al.  Nanotube molecular transporters: internalization of carbon nanotube-protein conjugates into Mammalian cells. , 2004, Journal of the American Chemical Society.

[12]  M. Prato,et al.  Translocation of bioactive peptides across cell membranes by carbon nanotubes. , 2004, Chemical communications.

[13]  S. Bose,et al.  Chemical functionalization of graphene and its applications , 2012 .

[14]  Chongwu Zhou,et al.  Review of chemical vapor deposition of graphene and related applications. , 2013, Accounts of chemical research.

[15]  Liming Nie,et al.  Structural and functional photoacoustic molecular tomography aided by emerging contrast agents. , 2014, Chemical Society reviews.

[16]  Hao Wang,et al.  One-step microwave-assisted polyol synthesis of green luminescent carbon dots as optical nanoprobes , 2014 .

[17]  Maurizio Prato,et al.  Double functionalization of carbon nanotubes for multimodal drug delivery. , 2006, Chemical communications.

[18]  Liang-shi Li,et al.  Large, solution-processable graphene quantum dots as light absorbers for photovoltaics. , 2010, Nano letters.

[19]  Huan-Cheng Chang,et al.  Bright fluorescent nanodiamonds: no photobleaching and low cytotoxicity. , 2005, Journal of the American Chemical Society.

[20]  E. Canto,et al.  Purified and Oxidized Single-Walled Carbon Nanotubes as Robust Near-IR Fluorescent Probes for Molecular Imaging , 2010 .

[21]  M. Prato,et al.  Intracellular Trafficking of Carbon Nanotubes by Confocal Laser Scanning Microscopy , 2007 .

[22]  Kevin Dhaliwal,et al.  Surface-enhanced Raman scattering in cancer detection and imaging. , 2013, Trends in biotechnology.

[23]  T. Ichihashi,et al.  Single-shell carbon nanotubes of 1-nm diameter , 1993, Nature.

[24]  S. C. O'brien,et al.  C60: Buckminsterfullerene , 1985, Nature.

[25]  Zhe Wang,et al.  Photosensitizer Loaded Nano-Graphene for Multimodality Imaging Guided Tumor Photodynamic Therapy , 2014, Theranostics.

[26]  N. Wu,et al.  Origin of strong excitation wavelength dependent fluorescence of graphene oxide. , 2014, ACS nano.

[27]  Darren J. Martin,et al.  THE BIOCOMPATIBILITY OF CARBON NANOTUBES , 2006 .

[28]  Zhuang Liu,et al.  Functionalization of carbon nanotubes via cleavable disulfide bonds for efficient intracellular delivery of siRNA and potent gene silencing. , 2005, Journal of the American Chemical Society.

[29]  Zhuang Liu,et al.  Carbon nanotubes as intracellular transporters for proteins and DNA: an investigation of the uptake mechanism and pathway. , 2006, Angewandte Chemie.

[30]  A. Krueger,et al.  Functionality is Key: Recent Progress in the Surface Modification of Nanodiamond , 2012 .

[31]  T. Maekawa,et al.  Quantum dot tailored to single wall carbon nanotubes: a multifunctional hybrid nanoconstruct for cellular imaging and targeted photothermal therapy. , 2014, Small.

[32]  Andrei E. Lugovtsov,et al.  The influence of nanodiamond on the oxygenation states and micro rheological properties of human red blood cells in vitro , 2012, Journal of biomedical optics.

[33]  M. Zheng,et al.  Fluorescence efficiency of individual carbon nanotubes. , 2007, Nano letters.

[34]  Dirk M. Guldi,et al.  Carbon nanotubes and related structures : synthesis, characterization, functionalization, and applications , 2010 .

[35]  Kai Yang,et al.  Optimization of surface chemistry on single-walled carbon nanotubes for in vivo photothermal ablation of tumors. , 2011, Biomaterials.

[36]  K. Müllen,et al.  Bottom-up fabrication of photoluminescent graphene quantum dots with uniform morphology. , 2011, Journal of the American Chemical Society.

[37]  H. Hong,et al.  Molecular Imaging with Single-Walled Carbon Nanotubes. , 2009, Nano today.

[38]  D. Guldi,et al.  Tuning and optimizing the intrinsic interactions between phthalocyanine-based PPV oligomers and single-wall carbon nanotubes toward n-type/p-type , 2011 .

[39]  Hsiao-Yun Wu,et al.  Characterization and application of single fluorescent nanodiamonds as cellular biomarkers , 2007, Proceedings of the National Academy of Sciences.

[40]  M. Prato,et al.  Phthalocyanine-pyrene conjugates: a powerful approach toward carbon nanotube solar cells. , 2010, Journal of the American Chemical Society.

[41]  H. Dai,et al.  High performance in vivo near-IR (>1 μm) imaging and photothermal cancer therapy with carbon nanotubes , 2010, Nano research.

[42]  Jiaqi Pan,et al.  Simple one-step synthesis of water-soluble fluorescent carbon dots from waste paper , 2014 .

[43]  T. Hertel,et al.  Quantum yield heterogeneities of aqueous single-wall carbon nanotube suspensions. , 2007, Journal of the American Chemical Society.

[44]  A. Hirsch,et al.  Chemistry with graphene and graphene oxide-challenges for synthetic chemists. , 2014, Angewandte Chemie.

[45]  Thomas M. Higgins,et al.  Scalable production of large quantities of defect-free few-layer graphene by shear exfoliation in liquids. , 2014, Nature materials.

[46]  Lei Guo,et al.  Cutting sp2clusters in graphene sheets into colloidal graphene quantum dots with strong green fluorescence , 2012 .

[47]  Bai Yang,et al.  Surface Chemistry Routes to Modulate the Photoluminescence of Graphene Quantum Dots: From Fluorescence Mechanism to Up‐Conversion Bioimaging Applications , 2012 .

[48]  V. C. Moore,et al.  Band Gap Fluorescence from Individual Single-Walled Carbon Nanotubes , 2002, Science.

[49]  Agnes B Kane,et al.  Biological interactions of graphene-family nanomaterials: an interdisciplinary review. , 2012, Chemical research in toxicology.

[50]  M. Herranz,et al.  The nano-forms of carbon , 2008 .

[51]  H. Choi,et al.  Effect of nucleases on the cellular internalization of fluorescent labeled DNA-functionalized single-walled carbon nanotubes , 2008 .

[52]  H. Dai,et al.  Soluble single-walled carbon nanotubes as longboat delivery systems for platinum(IV) anticancer drug design. , 2007, Journal of the American Chemical Society.

[53]  Liangzhu Feng,et al.  Photothermally enhanced photodynamic therapy delivered by nano-graphene oxide. , 2011, ACS nano.

[54]  M. Prato,et al.  Organic functionalisation and characterisation of single-walled carbon nanotubes. , 2009, Chemical Society reviews.

[55]  M. Yudasaka,et al.  Selective Production of Single-Wall Carbon Nanohorn Aggregates and Their Formation Mechanism , 2002 .

[56]  Anant Kumar Singh,et al.  Gold nano-popcorn attached SWCNT hybrid nanomaterial for targeted diagnosis and photothermal therapy of human breast cancer cells. , 2011, ACS applied materials & interfaces.

[57]  R. Weissleder A clearer vision for in vivo imaging , 2001, Nature Biotechnology.

[58]  J. Irudayaraj,et al.  Protein-directed reduction of graphene oxide and intracellular imaging. , 2011, Chemical communications.

[59]  N. Steinmetz,et al.  Fluorescent nanodiamonds embedded in biocompatible translucent shells. , 2014, Small.

[60]  Adriele Prina-Mello,et al.  Screening the cytotoxicity of single-walled carbon nanotubes using novel 3D tissue-mimetic models. , 2011, ACS nano.

[61]  Sailing He,et al.  Observation of multiphoton-induced fluorescence from graphene oxide nanoparticles and applications in in vivo functional bioimaging. , 2012, Angewandte Chemie.

[62]  S. Chiang,et al.  Fluorescent nanodiamonds for specifically targeted bioimaging: Application to the interaction of transferrin with transferrin receptor , 2009 .

[63]  John Yu,et al.  Tracking the engraftment and regenerative capabilities of transplanted lung stem cells using fluorescent nanodiamonds , 2013, Nature nanotechnology.

[64]  W. Wang,et al.  Quantum‐Dot‐Activated Luminescent Carbon Nanotubes via a Nano Scale Surface Functionalization for in vivo Imaging , 2007, Advanced Materials.

[65]  D. Guldi,et al.  Covalent and noncovalent phthalocyanine-carbon nanostructure systems: synthesis, photoinduced electron transfer, and application to molecular photovoltaics. , 2010, Chemical reviews.

[66]  Ganesh Gollavelli,et al.  Multi-functional graphene as an in vitro and in vivo imaging probe. , 2012, Biomaterials.

[67]  H. Wegner,et al.  Nano-rings with a handle – Synthesis of substituted cycloparaphenylenes , 2014, Beilstein journal of nanotechnology.

[68]  Ya‐Ping Sun,et al.  Quantum-sized carbon dots for bright and colorful photoluminescence. , 2006, Journal of the American Chemical Society.

[69]  Kunihiro Tsuchida,et al.  Fabrication of ZnPc/protein nanohorns for double photodynamic and hyperthermic cancer phototherapy , 2008, Proceedings of the National Academy of Sciences.

[70]  S. Yao,et al.  Efficient assembly of multi-walled carbon nanotube-CdSe/ZnS quantum dot hybrids with high biocompatibility and fluorescence property. , 2011, Colloids and surfaces. B, Biointerfaces.

[71]  Zhuang Liu,et al.  A route to brightly fluorescent carbon nanotubes for near-infrared imaging in mice. , 2009, Nature nanotechnology.

[72]  Fang Liu,et al.  Strongly green-photoluminescent graphene quantum dots for bioimaging applications. , 2011, Chemical communications.

[73]  K. Itami,et al.  Synthesis of cycloparaphenylenes and related carbon nanorings: a step toward the controlled synthesis of carbon nanotubes. , 2012, Accounts of chemical research.

[74]  Igor L. Medintz,et al.  Functionalizing nanoparticles with biological molecules: developing chemistries that facilitate nanotechnology. , 2013, Chemical reviews.

[75]  R. Kaner,et al.  Honeycomb carbon: a review of graphene. , 2010, Chemical reviews.

[76]  Cheng-Chun Chang,et al.  Fluorescent Nanodiamond – A Novel Nanomaterial for In Vivo Applications , 2011 .

[77]  Takeshi Azami,et al.  Toxicity of single-walled carbon nanohorns. , 2008, ACS nano.

[78]  T. Mustelin,et al.  Full-length single-walled carbon nanotubes decorated with streptavidin-conjugated quantum dots as multivalent intracellular fluorescent nanoprobes. , 2006, Biomacromolecules.

[79]  I. In,et al.  Temperature and pH-tunable fluorescence nanoplatform with graphene oxide and BODIPY-conjugated polymer for cell imaging and therapy. , 2013, Macromolecular rapid communications.

[80]  Maurizio Prato,et al.  Asbestos-like pathogenicity of long carbon nanotubes alleviated by chemical functionalization. , 2013, Angewandte Chemie.

[81]  M. S. de Vries,et al.  Cobalt-catalysed growth of carbon nanotubes with single-atomic-layer walls , 1993, Nature.

[82]  M. Ozkan,et al.  Nano-oncology: drug delivery, imaging, and sensing , 2006, Analytical and bioanalytical chemistry.

[83]  M. Otyepka,et al.  Functionalization of graphene: covalent and non-covalent approaches, derivatives and applications. , 2012, Chemical reviews.

[84]  J. Coleman Liquid exfoliation of defect-free graphene. , 2013, Accounts of chemical research.

[85]  D. Simionescu,et al.  Small noncytotoxic carbon nano-onions: first covalent functionalization with biomolecules. , 2010, Chemistry.

[86]  C. Rao,et al.  Graphene : synthesis, properties ,and phenomena , 2012 .

[87]  Zhuang Liu,et al.  Multiplexed five-color molecular imaging of cancer cells and tumor tissues with carbon nanotube Raman tags in the near-infrared , 2010, Nano research.

[88]  Omar K. Yaghi,et al.  In vivo fluorescence imaging in the second near-infrared window with long circulating carbon nanotubes capable of ultrahigh tumor uptake. , 2012, Journal of the American Chemical Society.

[89]  Richard Martel,et al.  Giant Raman scattering from J-aggregated dyes inside carbon nanotubes for multispectral imaging , 2013, Nature Photonics.

[90]  B. K. Gupta,et al.  Graphene quantum dots derived from carbon fibers. , 2012, Nano letters.

[91]  Xuwei Chen,et al.  Quantum dots conjugated with Fe3O4-filled carbon nanotubes for cancer-targeted imaging and magnetically guided drug delivery. , 2012, Langmuir : the ACS journal of surfaces and colloids.

[92]  Ivan Rehor,et al.  Designing the nanobiointerface of fluorescent nanodiamonds: highly selective targeting of glioma cancer cells. , 2015, Nanoscale.

[93]  J. Coleman,et al.  Debundling of single-walled nanotubes by dilution: observation of large populations of individual nanotubes in amide solvent dispersions. , 2006, The journal of physical chemistry. B.

[94]  J. Tour,et al.  Stepwise Quenching of Exciton Fluorescence in Carbon Nanotubes by Single-Molecule Reactions , 2007, Science.

[95]  S. Sonkar,et al.  Carbon nano-onions for imaging the life cycle of Drosophila melanogaster. , 2011, Small.

[96]  Kai Yang,et al.  Protamine Functionalized Single‐Walled Carbon Nanotubes for Stem Cell Labeling and In Vivo Raman/Magnetic Resonance/Photoacoustic Triple‐Modal Imaging , 2012 .

[97]  Michael S. Strano,et al.  Size-dependent cellular uptake and expulsion of single-walled carbon nanotubes: single particle tracking and a generic uptake model for nanoparticles. , 2009, ACS nano.

[98]  R. Smalley,et al.  Functionalization of carbon nanotubes by electrochemical reduction of aryl diazonium salts: a bucky paper electrode. , 2001, Journal of the American Chemical Society.

[99]  Li Cao,et al.  Photoluminescence properties of graphene versus other carbon nanomaterials. , 2013, Accounts of chemical research.

[100]  Elena Perevedentseva,et al.  Direct and in vitro observation of growth hormone receptor molecules in A549 human lung epithelial cells by nanodiamond labeling , 2007 .

[101]  Huan-Cheng Chang,et al.  Superresolution imaging of albumin-conjugated fluorescent nanodiamonds in cells by stimulated emission depletion. , 2011, Angewandte Chemie.

[102]  Ya‐Ping Sun,et al.  Bandgap-like strong fluorescence in functionalized carbon nanoparticles. , 2010, Angewandte Chemie.

[103]  R. Haddon,et al.  Nitric Acid Purification of Single-Walled Carbon Nanotubes , 2003 .

[104]  J. Coleman,et al.  Spontaneous debundling of single-walled carbon nanotubes in DNA-based dispersions , 2007 .

[105]  Kai Yang,et al.  Single-walled carbon nanotubes in biomedical imaging , 2011 .

[106]  S. Giordani,et al.  Carbon nano-onions (multi-layer fullerenes): chemistry and applications , 2014, Beilstein journal of nanotechnology.

[107]  M. Dresselhaus,et al.  Structure-Based Carbon Nanotube Sorting by Sequence-Dependent DNA Assembly , 2003, Science.

[108]  M. Prato,et al.  Luminescence of Functionalized Carbon Nanotubes as a Tool to Monitor Bundle Formation and Dissociation in Water: The Effect of Plasmid‐DNA Complexation , 2006 .

[109]  Sandeep Kumar Vashist,et al.  Interfacing carbon nanotubes with living mammalian cells and cytotoxicity issues. , 2010, Chemical research in toxicology.

[110]  P. Eklund,et al.  Vibrational modes of carbon nanotubes; Spectroscopy and theory , 1995 .

[111]  M. Prato,et al.  Targeting carbon nanotubes against cancer. , 2012, Chemical communications.

[112]  YuHuang Wang,et al.  Brightening of carbon nanotube photoluminescence through the incorporation of sp3 defects. , 2013, Nature chemistry.

[113]  Liming Dai,et al.  Nanodiamonds for nanomedicine. , 2009, Nanomedicine.

[114]  S. Bachilo,et al.  Oxygen Doping Modifies Near-Infrared Band Gaps in Fluorescent Single-Walled Carbon Nanotubes , 2010, Science.

[115]  M. C. Mancini,et al.  Bioimaging: second window for in vivo imaging. , 2009, Nature nanotechnology.

[116]  S. Shen,et al.  A simple one-step method to prepare fluorescent carbon dots and their potential application in non-invasive glioma imaging. , 2014, Nanoscale.

[117]  Steven A Curley,et al.  Mammalian pharmacokinetics of carbon nanotubes using intrinsic near-infrared fluorescence , 2006, Proceedings of the National Academy of Sciences.

[118]  Dean Ho,et al.  Multimodal Nanodiamond Drug Delivery Carriers for Selective Targeting, Imaging, and Enhanced Chemotherapeutic Efficacy , 2011, Advanced materials.

[119]  Klaus Müllen,et al.  A bottom-up approach from molecular nanographenes to unconventional carbon materials , 2008 .

[120]  Hongjie Dai,et al.  Carbon nanotubes: synthesis, integration, and properties. , 2002, Accounts of chemical research.

[121]  H. Niu,et al.  Cellular uptake and phototoxicity of surface-modified fluorescent nanodiamonds , 2012 .

[122]  Daniel O. Frimannsson,et al.  Azide conjugatable and pH responsive near-infrared fluorescent imaging probes. , 2009, Organic letters.

[123]  Barry Moran,et al.  Functionalization of carbon nanoparticles modulates inflammatory cell recruitment and NLRP3 inflammasome activation. , 2013, Small.

[124]  N. Jana,et al.  Carbohydrate coated, folate functionalized colloidal graphene as a nanocarrier for both hydrophobic and hydrophilic drugs. , 2014, Nanoscale.

[125]  Elena Perevedentseva,et al.  Nanodiamond for intracellular imaging in the microorganisms in vivo , 2012, Journal of biophotonics.

[126]  Atula S. D. Sandanayaka,et al.  Sensitive efficiency of photoinduced electron transfer to band gaps of semiconductive single-walled carbon nanotubes with supramolecularly attached zinc porphyrin bearing pyrene glues. , 2010, Journal of the American Chemical Society.

[127]  M. Prato,et al.  Electronically interacting single wall carbon nanotube–porphyrin nanohybrids , 2006 .

[128]  M. Brameshuber,et al.  Mapping the intracellular distribution of carbon nanotubes after targeted delivery to carcinoma cells using confocal Raman imaging as a label-free technique , 2012, Journal of physics. Condensed matter : an Institute of Physics journal.

[129]  Christopher G. Rylander,et al.  Single-walled carbon nanohorns decorated with semiconductor quantum dots to evaluate intracellular transport , 2014, Journal of nanoparticle research.

[130]  Huan-Cheng Chang,et al.  Nanodiamonds for optical bioimaging , 2010 .

[131]  Elena Perevedentseva,et al.  Nanometer-sized diamond particle as a probe for biolabeling. , 2007, Biophysical journal.

[132]  Hongjie Dai,et al.  siRNA delivery into human T cells and primary cells with carbon-nanotube transporters. , 2007, Angewandte Chemie.

[133]  J. Pinson,et al.  Covalent Modification of Carbon Surfaces by Aryl Radicals Generated from the Electrochemical Reduction of Diazonium Salts , 1997 .

[134]  M. Bawendi,et al.  Selection of Quantum Dot Wavelengths for Biomedical Assays and Imaging , 2003, Molecular Imaging.

[135]  M. Strano,et al.  Highly efficient exfoliation of individual single-walled carbon nanotubes by biocompatible phenoxylated dextran. , 2013, Nanoscale.

[136]  Jörg Opitz,et al.  Selective targeting of green fluorescent nanodiamond conjugates to mitochondria in HeLa cells , 2009, Journal of biophotonics.

[137]  Andrew S. Mount,et al.  RNA polymer translocation with single-walled carbon nanotubes , 2004 .

[138]  Hongjie Dai,et al.  Multiplexed multicolor Raman imaging of live cells with isotopically modified single walled carbon nanotubes. , 2008, Journal of the American Chemical Society.

[139]  S. Fukuzumi,et al.  Ordered assembly of protonated porphyrin driven by single-wall carbon nanotubes. J- and H-aggregates to nanorods. , 2005, Journal of the American Chemical Society.

[140]  P. Zeng,et al.  Synthesis of NaYF(4):Yb,Er/single-walled carbon nanohorns nanocomposite and its application as cells label. , 2012, Analytical biochemistry.

[141]  M. Prato,et al.  Organic functionalization and optical properties of carbon onions. , 2003, Journal of the American Chemical Society.

[142]  Anne Claire Dupuis,et al.  The catalyst in the CCVD of carbon nanotubes—a review , 2005 .

[143]  J. Boudou,et al.  Peptide‐Grafted Nanodiamonds: Preparation, Cytotoxicity and Uptake in Cells , 2008, Chembiochem : a European journal of chemical biology.

[144]  Kai Yang,et al.  Graphene in mice: ultrahigh in vivo tumor uptake and efficient photothermal therapy. , 2010, Nano letters.

[145]  Michael S Strano,et al.  M13 phage-functionalized single-walled carbon nanotubes as nanoprobes for second near-infrared window fluorescence imaging of targeted tumors. , 2012, Nano letters.

[146]  Nelson Durán,et al.  Nanotoxicity of graphene and graphene oxide. , 2014, Chemical research in toxicology.

[147]  N. Jux,et al.  Towards tunable graphene/phthalocyanine-PPV hybrid systems. , 2011, Angewandte Chemie.

[148]  Yanli Zhao,et al.  Graphene oxide wrapping on squaraine-loaded mesoporous silica nanoparticles for bioimaging. , 2012, Journal of the American Chemical Society.

[149]  M. Prato,et al.  Cellular uptake of functionalized carbon nanotubes is independent of functional group and cell type. , 2007, Nature nanotechnology.

[150]  Chunhai Fan,et al.  Intracellular imaging with a graphene-based fluorescent probe. , 2010, Small.

[151]  A. Chuvilin,et al.  Onion-like carbon from ultra-disperse diamond , 1994 .

[152]  Stanislaus S. Wong,et al.  Functionalized single-walled carbon nanotubes as rationally designed vehicles for tumor-targeted drug delivery. , 2008, Journal of the American Chemical Society.

[153]  Durairaj Baskaran,et al.  Carbon nanotubes with covalently linked porphyrin antennae: photoinduced electron transfer. , 2005, Journal of the American Chemical Society.

[154]  X. An,et al.  A novel rapid and green synthesis of highly luminescent carbon dots with good biocompatibility for cell imaging , 2014 .

[155]  Mingli Chen,et al.  Conjugation of quantum dots with graphene for fluorescence imaging of live cells. , 2011, The Analyst.

[156]  Jui‐I Chao,et al.  Covalent linkage of nanodiamond-paclitaxel for drug delivery and cancer therapy , 2010, Nanotechnology.

[157]  M. Dresselhaus,et al.  The big picture of Raman scattering in carbon nanotubes , 2007 .

[158]  Huan-Cheng Chang,et al.  The long-term stability and biocompatibility of fluorescent nanodiamond as an in vivo contrast agent. , 2012, Biomaterials.

[159]  Wei Wang,et al.  Graphene oxide noncovalent photosensitizer and its anticancer activity in vitro. , 2011, Chemistry.

[160]  S. Sahoo,et al.  Nanotech approaches to drug delivery and imaging. , 2003, Drug discovery today.

[161]  Kevin Welsher,et al.  Deep-tissue anatomical imaging of mice using carbon nanotube fluorophores in the second near-infrared window , 2011, Proceedings of the National Academy of Sciences.

[162]  S. Gambhir,et al.  Noninvasive Raman spectroscopy in living mice for evaluation of tumor targeting with carbon nanotubes. , 2008, Nano letters.

[163]  H. Dai,et al.  Carbon nanotubes as intracellular protein transporters: generality and biological functionality. , 2005, Journal of the American Chemical Society.

[164]  Weibo Cai,et al.  Circulation and long-term fate of functionalized, biocompatible single-walled carbon nanotubes in mice probed by Raman spectroscopy , 2008, Proceedings of the National Academy of Sciences.

[165]  C. Tung,et al.  Inside Cover: Graphene‐Supported Ultrafine Metal Nanoparticles Encapsulated by Mesoporous Silica: Robust Catalysts for Oxidation and Reduction Reactions (Angew. Chem. Int. Ed. 1/2014) , 2014 .

[166]  Yanjun Shi,et al.  Fluorescent graphene oxide composites synthesis and its biocompatibility study , 2012 .

[167]  M. Dresselhaus,et al.  Perspectives on carbon nanotubes and graphene Raman spectroscopy. , 2010, Nano letters.

[168]  W. Bollmann,et al.  Action of Graphite as a Lubricant , 1960, Nature.

[169]  R. Smalley,et al.  Structure-Assigned Optical Spectra of Single-Walled Carbon Nanotubes , 2002, Science.

[170]  I. Alexandrou,et al.  Characterisation of carbon nano-onions using Raman spectroscopy , 2003 .

[171]  Chunhai Fan,et al.  The Biocompatibility of Nanodiamonds and Their Application in Drug Delivery Systems , 2012, Theranostics.

[172]  Bai Yang,et al.  Bioimaging based on fluorescent carbon dots , 2014 .

[173]  R. Aitken,et al.  Carbon nanotubes: a review of their properties in relation to pulmonary toxicology and workplace safety. , 2006, Toxicological sciences : an official journal of the Society of Toxicology.

[174]  J. Rojo,et al.  Selective carbohydrate-lectin interactions in covalent graphene- and SWCNT-based molecular recognition systems , 2013 .

[175]  Li Cao,et al.  Competitive Performance of Carbon “Quantum” Dots in Optical Bioimaging , 2012, Theranostics.

[176]  Shouwu Guo,et al.  Folic Acid-conjugated Graphene Oxide loaded with Photosensitizers for Targeting Photodynamic Therapy , 2011, Theranostics.

[177]  Zhuyuan Wang,et al.  Optically encoded nanoprobes using single walled carbon nanotube as the building scaffold for magnetic field guided cell imaging. , 2014, Talanta.

[178]  Bai Yang,et al.  Highly photoluminescent carbon dots for multicolor patterning, sensors, and bioimaging. , 2013, Angewandte Chemie.

[179]  S. Gambhir,et al.  Noninvasive molecular imaging of small living subjects using Raman spectroscopy , 2008, Proceedings of the National Academy of Sciences.

[180]  Saber M Hussain,et al.  Are diamond nanoparticles cytotoxic? , 2007, The journal of physical chemistry. B.

[181]  Xiaoke Zhang,et al.  Targeted delivery and controlled release of doxorubicin to cancer cells using modified single wall carbon nanotubes. , 2009, Biomaterials.

[182]  François Treussart,et al.  Photoluminescent diamond nanoparticles for cell labeling: study of the uptake mechanism in mammalian cells. , 2009, ACS nano.

[183]  Kazuhiro Ikeda,et al.  Real-time background-free selective imaging of fluorescent nanodiamonds in vivo. , 2012, Nano letters.

[184]  S. Irle,et al.  Combined experimental and theoretical studies on the photophysical properties of cycloparaphenylenes. , 2012, Organic & biomolecular chemistry.

[185]  Zhuang Liu,et al.  Carbon nanotubes for biomedical imaging: the recent advances. , 2013, Advanced drug delivery reviews.

[186]  H. Dai,et al.  Noncovalent functionalization of carbon nanotubes by fluorescein-polyethylene glycol: supramolecular conjugates with pH-dependent absorbance and fluorescence. , 2007, Journal of the American Chemical Society.

[187]  H. Dai,et al.  Chirality enriched (12,1) and (11,3) single-walled carbon nanotubes for biological imaging. , 2012, Journal of the American Chemical Society.

[188]  Jacques Lefebvre,et al.  Photoluminescence imaging of suspended single-walled carbon nanotubes. , 2006, Nano letters.

[189]  S. Terakawa,et al.  Multi-color imaging of fluorescent nanodiamonds in living HeLa cells using direct electron-beam excitation. , 2014, Chemphyschem : a European journal of chemical physics and physical chemistry.

[190]  Yunchao Li,et al.  Surrounding media sensitive photoluminescence of boron-doped graphene quantum dots for highly fluorescent dyed crystals, chemical sensing and bioimaging , 2014 .

[191]  C. Bittencourt,et al.  Controlled carboxylic acid introduction: a route to highly purified oxidised single-walled carbon nanotubes , 2011 .

[192]  Hongjie Dai,et al.  Supramolecular Chemistry on Water- Soluble Carbon Nanotubes for Drug Loading and Delivery , 2007 .

[193]  Lin Zhou,et al.  Combination of chemotherapy and photodynamic therapy using graphene oxide as drug delivery system. , 2014, Journal of photochemistry and photobiology. B, Biology.

[194]  D. Edie,et al.  Reactivity differences between carbon nano onions (CNOs) prepared by different methods. , 2007, Chemistry, an Asian journal.

[195]  Seiichi Taruta,et al.  Safe Clinical Use of Carbon Nanotubes as Innovative Biomaterials , 2014, Chemical reviews.

[196]  Masaki Ozawa,et al.  A general procedure to functionalize agglomerating nanoparticles demonstrated on nanodiamond. , 2009, ACS nano.

[197]  J. Tour,et al.  Highly Functionalized Carbon Nanotubes Using in Situ Generated Diazonium Compounds , 2001 .

[198]  J. FRASER STODDART,et al.  Noncovalent functionalization of single-walled carbon nanotubes. , 2009, Accounts of chemical research.

[199]  X. Qu,et al.  Improvement of photoluminescence of graphene quantum dots with a biocompatible photochemical reduction pathway and its bioimaging application. , 2013, ACS applied materials & interfaces.

[200]  Pier Paolo Pompa,et al.  Super-resolution fluorescence imaging of biocompatible carbon dots. , 2014, Nanoscale.

[201]  Michael S Strano,et al.  Single-particle tracking of endocytosis and exocytosis of single-walled carbon nanotubes in NIH-3T3 cells. , 2008, Nano letters.

[202]  Andre K. Geim,et al.  Electric Field Effect in Atomically Thin Carbon Films , 2004, Science.

[203]  A. Jorio,et al.  Resonance Raman spectroscopy of the radial breathing modes in carbon nanotubes , 2010 .

[204]  L. Echegoyen,et al.  NIR fluorescence labelled carbon nano-onions: synthesis, analysis and cellular imaging. , 2014, Journal of materials chemistry. B.

[205]  Christopher G. Rylander,et al.  In vitro and in vivo studies of single-walled carbon nanohorns with encapsulated metallofullerenes and exohedrally functionalized quantum dots. , 2010, Nano letters.

[206]  B J McNeil,et al.  Advances in biomedical imaging. , 2001, JAMA.

[207]  S. Sonkar,et al.  Carbon Nano-Onions as Nontoxic and High-Fluorescence Bioimaging Agent in Food Chain—An In Vivo Study from Unicellular E. coli to Multicellular C. elegans , 2012 .

[208]  Kwangmeyung Kim,et al.  Nanoprobes for biomedical imaging in living systems , 2011 .

[209]  M. Nesladek,et al.  Boosting nanodiamond fluorescence: towards development of brighter probes. , 2013, Nanoscale.

[210]  Ya‐Ping Sun,et al.  Carbon dots for multiphoton bioimaging. , 2007, Journal of the American Chemical Society.

[211]  Zhuang Liu,et al.  Drug delivery with carbon nanotubes for in vivo cancer treatment. , 2008, Cancer research.

[212]  Derrick Dean,et al.  Nanodiamond-DGEA peptide conjugates for enhanced delivery of doxorubicin to prostate cancer , 2014, Beilstein journal of nanotechnology.

[213]  Suzy V. Torti,et al.  Hybrid 2D Nanomaterials as Dual‐Mode Contrast Agents in Cellular Imaging , 2012, Advanced materials.

[214]  M. I. Katsnelson,et al.  Chaotic Dirac Billiard in Graphene Quantum Dots , 2007, Science.

[215]  A. S. Moses,et al.  Imaging and drug delivery using theranostic nanoparticles. , 2010, Advanced drug delivery reviews.

[216]  C. Chiang,et al.  Preparation of fluorescent magnetic nanodiamonds and cellular imaging. , 2008, Journal of the American Chemical Society.

[217]  R. Weisman,et al.  Single-walled carbon nanotubes in the intact organism: near-IR imaging and biocompatibility studies in Drosophila. , 2007, Nano letters.

[218]  Zhuang Liu,et al.  Noble metal coated single-walled carbon nanotubes for applications in surface enhanced Raman scattering imaging and photothermal therapy. , 2012, Journal of the American Chemical Society.

[219]  T. Xia,et al.  Toxic Potential of Materials at the Nanolevel , 2006, Science.

[220]  C. Cheng,et al.  Nanodiamond internalization in cells and the cell uptake mechanism , 2013, Journal of Nanoparticle Research.

[221]  Patrick Georges,et al.  Detection of single photoluminescent diamond nanoparticles in cells and study of the internalization pathway. , 2008, Small.

[222]  M. Prato,et al.  A carbon nano-onion-ferrocene donor-acceptor system: synthesis, characterization and properties. , 2009, Chemistry.

[223]  M. Yudasaka,et al.  Nano-aggregates of single-walled graphitic carbon nano-horns , 1999 .

[224]  Jason E. Riggs,et al.  Strong Luminescence of Solubilized Carbon Nanotubes , 2000 .

[225]  C. Bittencourt,et al.  Synthesis and characterization of boron azadipyrromethene single-wall carbon nanotube electron donor-acceptor conjugates. , 2011, ACS nano.

[226]  Patrick A. Cooke,et al.  Molecular Characterization of the Cytotoxic Mechanism of Multiwall Carbon Nanotubes and Nano-onions on Human Skin Fibroblast , 2005 .

[227]  Tingting Zheng,et al.  Green and facile synthesis of highly biocompatible graphene nanosheets and its application for cellular imaging and drug delivery , 2011 .

[228]  Pascal Aubert,et al.  High yield fabrication of fluorescent nanodiamonds , 2009, Nanotechnology.

[229]  Thomas E. Eurell,et al.  Single‐Walled Carbon Nanotube Spectroscopy in Live Cells: Towards Long‐Term Labels and Optical Sensors , 2005 .

[230]  Craig A. Poland,et al.  Carbon nanotubes introduced into the abdominal cavity of mice show asbestos-like pathogenicity in a pilot study. , 2008, Nature nanotechnology.

[231]  S. Bachilo,et al.  Near-infrared fluorescence microscopy of single-walled carbon nanotubes in phagocytic cells. , 2004, Journal of the American Chemical Society.

[232]  Yang Tian,et al.  Carbon Dot‐Based Inorganic–Organic Nanosystem for Two‐Photon Imaging and Biosensing of pH Variation in Living Cells and Tissues , 2012, Advanced materials.

[233]  Thomas Meinhardt,et al.  Pushing the Functionality of Diamond Nanoparticles to New Horizons: Orthogonally Functionalized Nanodiamond Using Click Chemistry , 2011 .

[234]  E. Rodríguez-Castellón,et al.  Carbon dots obtained using hydrothermal treatment of formaldehyde. Cell imaging in vitro. , 2014, Nanoscale.

[235]  Hongjie Dai,et al.  Protein microarrays with carbon nanotubes as multicolor Raman labels , 2008, Nature Biotechnology.

[236]  S. Iijima Helical microtubules of graphitic carbon , 1991, Nature.

[237]  Huan-Cheng Chang,et al.  Mass production and dynamic imaging of fluorescent nanodiamonds. , 2008, Nature nanotechnology.

[238]  Xiaoling Yang,et al.  Graphene quantum dots: emergent nanolights for bioimaging, sensors, catalysis and photovoltaic devices. , 2012, Chemical communications.

[239]  Igor L. Medintz,et al.  Quantum Dots in Bioanalysis: A Review of Applications across Various Platforms for Fluorescence Spectroscopy and Imaging , 2013, Applied spectroscopy.

[240]  Ching-Fang Chang,et al.  The exocytosis of fluorescent nanodiamond and its use as a long-term cell tracker. , 2011, Small.

[241]  Jason E. Riggs,et al.  Visible luminescence of carbon nanotubes and dependence on functionalization. , 2005, The journal of physical chemistry. B.

[242]  A. Goga,et al.  Nanodiamond Therapeutic Delivery Agents Mediate Enhanced Chemoresistant Tumor Treatment , 2011, Science Translational Medicine.

[243]  Kostas Kostarelos,et al.  The long and short of carbon nanotube toxicity , 2008, Nature Biotechnology.

[244]  A. Demchenko,et al.  Fluorescent carbon nanomaterials: "quantum dots" or nanoclusters? , 2014, Physical chemistry chemical physics : PCCP.

[245]  Kuang-Kai Liu,et al.  Endocytic carboxylated nanodiamond for the labeling and tracking of cell division and differentiation in cancer and stem cells. , 2009, Biomaterials.

[246]  Ying Fu,et al.  Facile synthesis of water-soluble, highly fluorescent graphene quantum dots as a robust biological label for stem cells , 2012 .

[247]  Yury Gogotsi,et al.  The properties and applications of nanodiamonds. , 2011, Nature nanotechnology.

[248]  Yun Lu,et al.  Facile route to highly photoluminescent carbon nanodots for ion detection, pH sensors and bioimaging. , 2014, Nanoscale.

[249]  N. S. Gajbhiye,et al.  Carbogenic nanodots: photoluminescence and room-temperature ferromagnetism. , 2011, Chemphyschem : a European journal of chemical physics and physical chemistry.

[250]  James F Rusling,et al.  Targeted killing of cancer cells in vivo and in vitro with EGF-directed carbon nanotube-based drug delivery. , 2009, ACS nano.

[251]  Chang Ming Li,et al.  One-step and high yield simultaneous preparation of single- and multi-layer graphene quantum dots from CX-72 carbon black , 2012 .

[252]  Guosong Hong,et al.  Multifunctional in vivo vascular imaging using near-infrared II fluorescence , 2012, Nature Medicine.

[253]  Lei Tao,et al.  Size tunable fluorescent nano-graphite oxides: preparation and cell imaging applications. , 2013, Physical chemistry chemical physics : PCCP.

[254]  H. Dai,et al.  Targeted single-wall carbon nanotube-mediated Pt(IV) prodrug delivery using folate as a homing device. , 2008, Journal of the American Chemical Society.

[255]  Navid B. Saleh,et al.  Tracking and quantification of single-walled carbon nanotubes in fish using near infrared fluorescence. , 2014, Environmental science & technology.

[256]  V. V. Danilenko,et al.  On the history of the discovery of nanodiamond synthesis , 2004 .

[257]  D. Ugarte Curling and closure of graphitic networks under electron-beam irradiation , 1992, Nature.

[258]  M. Prato,et al.  Targeted delivery of amphotericin B to cells by using functionalized carbon nanotubes. , 2005, Angewandte Chemie.

[259]  Zhuang Liu,et al.  Selective probing and imaging of cells with single walled carbon nanotubes as near-infrared fluorescent molecules. , 2008, Nano letters.

[260]  J. McFadden,et al.  Triple functionalisation of single-walled carbon nanotubes with doxorubicin, a monoclonal antibody, and a fluorescent marker for targeted cancer therapy , 2009 .

[261]  Anna Jagusiak,et al.  Carbon nanotubes for delivery of small molecule drugs. , 2013, Advanced drug delivery reviews.

[262]  Phaedon Avouris,et al.  Carbon-nanotube photonics and optoelectronics , 2008 .

[263]  V. Biju,et al.  Delivering quantum dots to cells: bioconjugated quantum dots for targeted and nonspecific extracellular and intracellular imaging. , 2010, Chemical Society reviews.

[264]  Thierry Gacoin,et al.  Nanodiamond as a vector for siRNA delivery to Ewing sarcoma cells. , 2011, Small.

[265]  H. Dai,et al.  Carbon nanotubes as multifunctional biological transporters and near-infrared agents for selective cancer cell destruction. , 2005, Proceedings of the National Academy of Sciences of the United States of America.

[266]  D. Guldi,et al.  Electron-donating behavior of few-layer graphene in covalent ensembles with electron-accepting phthalocyanines. , 2014, Journal of the American Chemical Society.

[267]  J. James,et al.  A Review of Carbon Nanotube Toxicity and Assessment of Potential Occupational and Environmental Health Risks , 2006, Critical reviews in toxicology.

[268]  K. Novoselov,et al.  Making graphene luminescent by oxygen plasma treatment. , 2009, ACS nano.

[269]  Omar K. Yaghi,et al.  Ultra-low doses of chirality sorted (6,5) carbon nanotubes for simultaneous tumor imaging and photothermal therapy. , 2013, ACS nano.

[270]  L. Echegoyen,et al.  Functionalization of multilayer fullerenes (carbon nano-onions) using diazonium compounds and "click" chemistry. , 2010, Organic letters.

[271]  Huan-Cheng Chang,et al.  In vivo imaging and toxicity assessments of fluorescent nanodiamonds in Caenorhabditis elegans. , 2010, Nano letters.

[272]  H. Dai,et al.  Ultrasmall reduced graphene oxide with high near-infrared absorbance for photothermal therapy. , 2011, Journal of the American Chemical Society.

[273]  Haeshin Lee,et al.  Photo- and pH-tunable multicolor fluorescent nanoparticle-based spiropyran- and BODIPY-conjugated polymer with graphene oxide. , 2014, Chemistry - An Asian Journal.

[274]  Jui‐I Chao,et al.  Cancer cell labeling and tracking using fluorescent and magnetic nanodiamond. , 2012, Biomaterials.

[275]  Fred Wudl,et al.  Carbon allotropes: beyond graphite and diamond , 2007 .

[276]  Martin M. F. Choi,et al.  Red-green-blue fluorescent hollow carbon nanoparticles isolated from chromatographic fractions for cellular imaging. , 2014, Nanoscale.