Noncovalent functionalization of single-walled carbon nanotubes.

Single-walled carbon nanotubes (SWNTs) have attracted much attention on account of their potential to be transformed into new materials that can be employed to address a wide range of applications. The insolubility of the SWNTs in most solvents and the difficulties of handling these highly intractable carbon nanostructures, however, are restricting their real-life applications at the present time. To improve upon the properties of the SWNTs, low-cost and industrially feasible approaches to their modifications are constantly being sought by chemists and materials scientists. Together, they have shown that noncovalent functionalization of the SWNTs can do much to preserve the desired properties of the SWNTs while remarkably improving their solubilities. This Account describes recent advances in the design, synthesis, and characterization of SWNT hybrids and evaluates applications of these new hybrid materials based on noncovalently functionalized SWNTs. Their solubilization enables the characterization of these hybrids as well as the investigation of the properties of the SWNTs using solution-based techniques. Cognizant of the structural properties of the functional molecules on the SWNTs, we present some of the recent work carried out by ourselves and others under the umbrella of the following three subtopics: (i) aromatic small-molecule-based noncovalent functionalization, (ii) biomacromolecule-based noncovalent functionalization, and (iii) polymer-based noncovalent functionalization. Several examples for the applications of noncovalently functionalized SWNT hybrids in the fabrication of field-effect transistor (FET) devices, chemical sensors, molecular switch tunnel junctions (MSTJs), and photovoltaic devices are highlighted and discussed. The blossoming of new methods for the noncovalent functionalization of the SWNTs promises a new generation of SWNT hybrid-based integrated multifunctional sensors and devices, an outcome which is essential for the development of carbon nanotube chemistry that interfaces with physics, materials, biology, and medical science.

[1]  M. Prato,et al.  Integrating single-wall carbon nanotubes into donor-acceptor nanohybrids. , 2004, Angewandte Chemie.

[2]  H. Byrne,et al.  Bundling and diameter selectivity in HiPco SWNTs poly(p-phenylene vinylene-co-2,5-dioctyloxy-m-phenylene vinylene) composites. , 2006, The journal of physical chemistry. B.

[3]  M. Prato,et al.  Carbon nanotubes in electron donor-acceptor nanocomposites. , 2005, Accounts of chemical research.

[4]  J. Fraser Stoddart,et al.  Preparation and Properties of Polymer-Wrapped Single-Walled Carbon Nanotubes , 2001 .

[5]  Taro Kimura,et al.  Single-walled carbon nanotubes acquire a specific lectin-affinity through supramolecular wrapping with lactose-appended schizophyllan. , 2004, Chemical communications.

[6]  J. F. Stoddart,et al.  A [2]Catenane-Based Solid State Electronically Reconfigurable Switch , 2000 .

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

[8]  Eric S. Snow,et al.  Chemical Vapor Detection Using Single-Walled Carbon Nanotubes , 2006 .

[9]  J. F. Stoddart,et al.  Noncovalent Side-Wall Functionalization of Single-Walled Carbon Nanotubes , 2003 .

[10]  W. E. Billups,et al.  Fluorination of single-wall carbon nanotubes and subsequent derivatization reactions. , 2002, Accounts of chemical research.

[11]  K. Sakurai,et al.  Inclusion of cut and as-grown single-walled carbon nanotubes in the helical superstructure of schizophyllan and curdlan (beta-1,3-glucans). , 2005, Journal of the American Chemical Society.

[12]  J. F. Stoddart,et al.  Single-walled carbon nanotubes under the influence of dynamic coordination and supramolecular chemistry. , 2005, Small.

[13]  K. Balasubramanian,et al.  Chemically functionalized carbon nanotubes. , 2005, Small.

[14]  Hsian-Rong Tseng,et al.  Single-walled carbon nanotube based molecular switch tunnel junctions. , 2003, Chemphyschem : a European journal of chemical physics and physical chemistry.

[15]  S. Shinkai,et al.  Hierarchical carbon nanotube assemblies created by sugar-boric or boronic acid interactions. , 2008, Chemical communications.

[16]  M. Prato,et al.  Spectroscopic characterization of photolytically generated radical ion pairs in single-wall carbon nanotubes bearing surface-immobilized tetrathiafulvalenes. , 2008, Journal of the American Chemical Society.

[17]  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.

[18]  J. F. Stoddart,et al.  Interactions between Conjugated Polymers and Single-Walled Carbon Nanotubes , 2002 .

[19]  Andreas Hirsch,et al.  Sidewall Functionalization of Carbon Nanotubes. , 2001, Angewandte Chemie.

[20]  Francesco Zerbetto,et al.  Interactions in single wall carbon nanotubes/pyrene/porphyrin nanohybrids. , 2006, Journal of the American Chemical Society.

[21]  K. Sakurai,et al.  Instantaneous inclusion of a polynucleotide and hydrophobic guest molecules into a helical core of cationic beta-1,3-glucan polysaccharide. , 2007, Journal of the American Chemical Society.

[22]  J. F. Stoddart,et al.  Light‐Induced Charge Transfer in Pyrene/CdSe‐SWNT Hybrids , 2008 .

[23]  A. Adronov,et al.  Noncovalent functionalization and solubilization of carbon nanotubes by using a conjugated Zn-porphyrin polymer. , 2006, Chemistry.

[24]  J. F. Stoddart,et al.  A tunable photosensor. , 2008, Journal of the American Chemical Society.

[25]  Maurizio Prato,et al.  Functionalized Carbon Nanotubes in Drug Design and Discovery , 2008 .

[26]  M. Meador,et al.  Wrapping of single-walled carbon nanotubes by a pi-conjugated polymer: the role of polymer conformation-controlled size selectivity. , 2008, The journal of physical chemistry. B.

[27]  David L. Carroll,et al.  A Composite from Poly(m‐phenylenevinylene‐co‐2,5‐dioctoxy‐p‐phenylenevinylene) and Carbon Nanotubes: A Novel Material for Molecular Optoelectronics , 1998 .

[28]  M. Strano,et al.  Reversible control of carbon nanotube aggregation for a glucose affinity sensor. , 2006, Angewandte Chemie.

[29]  R. Andrews,et al.  Multiwall Carbon Nanotubes: Synthesis and Application , 2003 .

[30]  H. Dai,et al.  Noncovalent sidewall functionalization of single-walled carbon nanotubes for protein immobilization. , 2001, Journal of the American Chemical Society.

[31]  J. F. Stoddart,et al.  Bioinspired detection of light using a porphyrin-sensitized single-wall nanotube field effect transistor. , 2006, Nano letters.

[32]  Ayumi Ishibashi,et al.  Individual dissolution of single-walled carbon nanotubes in aqueous solutions of steroid or sugar compounds and their Raman and near-IR spectral properties. , 2006, Chemistry.

[33]  J. Baldwin,et al.  Solubilization of single-wall carbon nanotubes by supramolecular encapsulation of helical amylose. , 2003, Journal of the American Chemical Society.

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

[35]  Hongjie Dai,et al.  Carbon Nanotubes: Synthesis, Integration, and Properties , 2003 .

[36]  Jinlin Huang,et al.  Fundamental Electronic Properties and Applications of Single-Walled Carbon Nanotubes , 2003 .

[37]  Lei Zhang.  Functionalization of single walled carbon nanotubes , 2006 .

[38]  S. Shinkai,et al.  Creation of hierarchical carbon nanotube assemblies through alternative packing of complementary semi-artificial beta-1,3-glucan/carbon nanotube composites. , 2008, Chemistry.

[39]  James R Heath,et al.  Starched carbon nanotubes. , 2002, Angewandte Chemie.

[40]  J. Deen,et al.  Supramolecular Functionalization of Single-Walled Carbon Nanotubes with Conjugated Polyelectrolytes and Their Patterning on Surfaces , 2008 .

[41]  Mark E. Thompson,et al.  Synthesis and Electronic Properties of Individual Single‐Walled Carbon Nanotube/Polypyrrole Composite Nanocables , 2005 .

[42]  J. F. Stoddart,et al.  Dispersion and Solubilization of Single-Walled Carbon Nanotubes with a Hyperbranched Polymer , 2002 .

[43]  W. Kutner,et al.  Water solubilization, determination of the number of different types of single-wall carbon nanotubes and their partial separation with respect to diameters by complexation with eta-cyclodextrin. , 2003, Chemical communications.

[44]  M. Prato,et al.  Chemistry of carbon nanotubes. , 2006, Chemical reviews.

[45]  Qing Zhang,et al.  Individually Dispersing Single-Walled Carbon Nanotubes with Novel Neutral pH Water-Soluble Chitosan Derivatives , 2008 .

[46]  Douglas R. Kauffman,et al.  Electronically Monitoring Biological Interactions with Carbon Nanotube Field‐Effect Transistors , 2008 .

[47]  Hugh J. Byrne,et al.  Characterization of the interaction of gamma cyclodextrin with single-walled carbon nanotubes , 2003 .

[48]  H. Dai,et al.  Phospholipid-dextran with a single coupling point: a useful amphiphile for functionalization of nanomaterials. , 2009, Journal of the American Chemical Society.

[49]  J. F. Stoddart,et al.  Pyrenecyclodextrin‐Decorated Single‐Walled Carbon Nanotube Field‐Effect Transistors as Chemical Sensors , 2008 .