Comparation of multiple terminal functional groups dendrimer silicon(IV) phthalocyanines: Photoinduced electron/energy transfer and electrochemical properties

Abstract Three novel aryl benzyl ether dendrimer silicon(IV) phthalocyanines with nitro/cyano/ether terminal functional groups were synthesized. The structures of these compounds were characterized by elemental analysis, IR, 1H NMR, thermogravimetric analysis and MALDI-TOF mass spectroscopic data. Photophysical properties, photoinduced intermolecular electron transfer constants, and photoinduced intramolecular energy transfer efficacies of three dendrimer silicon(IV) phthalocyanines were compared by UV/vis and fluorescence spectroscopic methods. The electrochemical behaviors of these dendrimer silicon(IV) phthalocyanines were studied by cyclic voltammetry (CV) and square wave voltammetry (SWV) measurements. Dendrimer silicon(IV) phthalocyanine with nitro groups exhibited the highest light harvesting ability, fluorescence quantum yields, and photoinduced intramolecular energy transfer efficacy. Our study suggests that this novel dendrimer silicon(IV) phthalocyanine is an effective energy transmission complex with high efficiency, and could be used as a potential light-harvesting system.

[1]  D. Russell,et al.  Targeting the oncofetal Thomsen-Friedenreich disaccharide using jacalin-PEG phthalocyanine gold nanoparticles for photodynamic cancer therapy. , 2012, Angewandte Chemie.

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

[3]  J. Meiss,et al.  Fluorinated Zinc Phthalocyanine as Donor for Efficient Vacuum‐Deposited Organic Solar Cells , 2012 .

[4]  Efficient passivated phthalocyanine-quantum dot solar cells. , 2015, Chemical communications.

[5]  Takuzo Aida,et al.  Dendrimer porphyrins and phthalocyanines. , 2009, Chemical reviews.

[6]  Paul Heremans,et al.  Structural evolution of evaporated lead phthalocyanine thin films for near-infrared sensitive solar cells , 2011 .

[7]  T. Torres,et al.  Microenvironment-switchable singlet oxygen generation by axially-coordinated hydrophilic ruthenium phthalocyanine dendrimers. , 2011, Physical chemistry chemical physics : PCCP.

[8]  Malcolm E. Kenney,et al.  Dichloro(phthalocyanino)silicon , 1965 .

[9]  Mm Martijn Wienk,et al.  Functionalized dendritic oligothiophenes: ruthenium phthalocyanine complexes and their application in bulk heterojunction solar cells. , 2009, Journal of the American Chemical Society.

[10]  A. Sorokin.  Phthalocyanine metal complexes in catalysis. , 2013, Chemical reviews.

[11]  Mei-Rong Ke,et al.  A non-aggregated and tumour-associated macrophage-targeted photosensitiser for photodynamic therapy: a novel zinc(II) phthalocyanine containing octa-sulphonates. , 2015, Chemical communications.

[12]  P. Ceroni,et al.  A molecular clip throws new light on the complexes formed by a family of cyclam-cored dendrimers with Zn(II) ions. Efficient energy transfer in the heteroleptic complexes. , 2011, Dalton transactions.

[13]  Neil B. McKeown,et al.  Phthalocyanine-centred aryl ether dendrimers with oligo(ethyleneoxy) surface groups , 2001 .

[14]  T. Arai,et al.  Photoisomerization and energy transfer in naphthalene-terminated stilbene dendrimers , 2012, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[15]  A. Beeby,et al.  Synthesis of novel phthalocyanine-tetrathiafulvalene hybrids; intramolecular fluorescence quenching related to molecular geometry. , 2002, The Journal of organic chemistry.

[16]  V. Ahsen,et al.  Comparative studies of photophysical and photochemical properties of solketal substituted platinum(II) and zinc(II) phthalocyanine sets , 2010 .

[17]  M. Grätzel.  Dye-sensitized solar cells , 2003 .

[18]  K. Yamaguchi,et al.  Mechanistic investigation of energy transfer in perylene-cored anthracene dendrimers , 2008 .

[19]  Malcolm E. Kenney,et al.  Deep penetration of a PDT drug into tumors by noncovalent drug-gold nanoparticle conjugates. , 2011, Journal of the American Chemical Society.

[20]  Hiroaki Horiuchi,et al.  Singlet molecular oxygen generation by water-soluble phthalocyanine dendrimers with different aggregation behavior , 2011 .

[21]  Matthew K. Hulvey,et al.  Detecting thiols in a microchip device using micromolded carbon ink electrodes modified with cobalt phthalocyanine. , 2006, The Analyst.

[22]  J. Fréchet,et al.  Synthesis and Steady-State Photophysical Properties of Dye-Labeled Dendrimers Having Novel Oligothiophene Cores: A Comparative Study , 2000 .

[23]  S. Fukuzumi,et al.  Proton-coupled electron-transfer reduction of dioxygen catalyzed by a saddle-distorted cobalt phthalocyanine. , 2012, Journal of the American Chemical Society.

[24]  T. Arai,et al.  The use of dendrimers as high-performance shells for round-trip energy transfer: efficient trans-cis photoisomerization from an excited triplet state produced within a dendrimer shell , 2011, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[25]  Yi Li,et al.  Artificial photosynthesis dendrimers integrating light-harvesting, electron delivery and hydrogen production , 2015 .

[26]  N. McKeown,et al.  The synthesis and glass-forming properties of phthalocyanine-containing poly(aryl ether) dendrimers. , 2000, Chemistry.

[27]  Dongxue Han,et al.  Enhanced Catalytic Performance of Pt-Free Iron Phthalocyanine by Graphene Support for Efficient Oxygen Reduction Reaction , 2013 .

[28]  T. Swager,et al.  Liquid-Crystalline Heterocyclic Phthalocyanine Analogues Based on Thiophene , 1997 .

[29]  Yiru Peng,et al.  The synthesis and photophysical properties of zinc (II) phthalocyanine bearing poly(aryl benzyl ether) dendritic substituents , 2010 .

[30]  A. Caminade,et al.  Octasubstituted metal-free phthalocyanine as core of phosphorus dendrimers: a probe for the properties of the internal structure. , 2005, Journal of the American Chemical Society.

[31]  R. Hatton,et al.  Organic Photovoltaic Devices Based on Water-Soluble Copper Phthalocyanine , 2011 .

[32]  Suzanne Fery-Forgues,et al.  ARE FLUORESCENCE QUANTUM YIELDS SO TRICKY TO MEASURE? A DEMONSTRATION USING FAMILIAR STATIONERY PRODUCTS , 1999 .

[33]  Dennis K. P. Ng,et al.  Dendritic phthalocyanines: synthesis, photophysical properties, and aggregation behavior , 2003 .

[34]  Takahiro Nomoto,et al.  Disulfide crosslinked polyion complex micelles encapsulating dendrimer phthalocyanine directed to improved efficiency of photodynamic therapy. , 2011, Journal of controlled release : official journal of the Controlled Release Society.

[35]  D. Ng,et al.  A dual activatable photosensitizer toward targeted photodynamic therapy. , 2014, Journal of medicinal chemistry.

[36]  SonBinh T. Nguyen,et al.  Porous organic polymers in catalysis: Opportunities and challenges , 2011 .

[37]  Dae Won Cho,et al.  A detailed investigation of light-harvesting efficiency of blue color emitting divergent iridium dendrimers with peripheral phenylcarbazole units. , 2014, Physical chemistry chemical physics : PCCP.

[38]  C. Whitehurst,et al.  The biology of photodynamic therapy. , 1997, Physics in medicine and biology.

[39]  Britt A. Minch,et al.  Octakis(2-benzyloxyethylsulfanyl) Copper (II) Phthalocyanine: A New Liquid Crystalline Discotic Material with Benzyl-Terminated, Thioether-Linked Side Chains , 2005 .

[40]  Shayu Li,et al.  Light-harvesting and photoisomerization in benzophenone and norbornadiene-labeled poly(aryl ether) dendrimers via intramolecular triplet energy transfer. , 2005, Journal of the American Chemical Society.

[41]  Mustafa Bulut,et al.  Peripheral octa-substituted metal-free, cobalt(II) and zinc(II) phthalocyanines bearing coumarin and chloro groups: Synthesis, characterization, spectral and electrochemical properties , 2012 .

[42]  N. Periasamy,et al.  Electron-transfer distance in intermolecular diffusion-limited reactions , 1991 .

[43]  Y. Yamaguchi,et al.  Dendritic metallophthalocyanines: synthesis and characterization of a zinc(ii) phthalocyanine[8]3-arborol , 1997 .

[44]  Chi Wu,et al.  Encapsulation of phthalocyanines in biodegradable poly(sebacic anhydride) nanoparticles , 2002 .

[45]  E. Durantini,et al.  Synthesis, properties, and photodynamic inactivation of Escherichia coli using a cationic and a noncharged Zn(II) pyridyloxyphthalocyanine derivatives. , 2005, Bioorganic & medicinal chemistry.

[46]  David Phillips,et al.  Excited singlet and triplet state electron-transfer reactions of aluminium(III) sulphonated phthalocyanine , 1982 .

[47]  H. Tam,et al.  Highly selective mitochondria-targeting amphiphilic silicon(IV) phthalocyanines with axially ligated rhodamine B for photodynamic therapy. , 2012, Inorganic chemistry.

[48]  A. L. Thompson,et al.  Energy and electron transfer in bifunctional non-conjugated dendrimers. , 2005, Journal of the American Chemical Society.

[49]  Jean M. J. Fréchet,et al.  Unsymmetrical three-dimensional macromolecules: preparation and characterization of strongly dipolar dendritic macromolecules , 1993 .

[50]  N. McKeown,et al.  Silicon Phthalocyanines with Axial Dendritic Substituents. , 1998, Angewandte Chemie.

[51]  Hongqin Yang,et al.  Photoinduced intra-molecular energy transfer in a novel zinc (II) phthalocyanine bearing poly (aryl benzyl ether) dendritic substituents , 2013 .

[52]  D. Seferos,et al.  Bis(tri-n-hexylsilyl oxide) silicon phthalocyanine: a unique additive in ternary bulk heterojunction organic photovoltaic devices. , 2014, ACS applied materials & interfaces.

[53]  M. El-Khouly,et al.  Silicon-phthalocyanine-cored fullerene dendrimers: synthesis and prolonged charge-separated states with dendrimer generations. , 2007, Chemistry.

[54]  David L. Andrews,et al.  Virtual photons, dipole fields and energy transfer: a quantum electrodynamical approach , 2004 .

[55]  A. Koca,et al.  The synthesis, characterization, electrochemical and spectroelectrochemical properties of a novel, cationic, water-soluble Zn phthalocyanine with extended conjugation , 2011 .

[56]  C. Lee,et al.  High‐Temperature Ferromagnetism of a Discotic Liquid Crystal Dilutely Intercalated with Iron(III) Phthalocyanine , 2010, Advanced materials.

[57]  N. S. Sariciftci,et al.  Supramolecular Association of Pyrrolidinofullerenes Bearing Chelating Pyridyl Groups and Zinc Phthalocyanine for Organic Solar Cells , 2007 .