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Pure Appl. Chem., 2003, Vol. 75, No. 8, pp. 1069-1075

http://dx.doi.org/10.1351/pac200375081069

Molecular porphyrin­fullerene architectures

D. M. Guldi

Radiation Laboratory, University of Notre Dame, IN 46556, USA

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  • Ray Anamika, Pal Haridas, Bhattacharya Sumanta: Photophysical investigations on supramolecular fullerene/phthalocyanine charge transfer interactions in solution. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2014, 117, 686. <http://dx.doi.org/10.1016/j.saa.2013.08.107>
  • Ghosh B.K., Bauri A., Bhattacharya S., Banerjee S.: Photophysical investigations on effective and selective complexation of a designed monoporhyrin with C60 and C70 in solution. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2014, 125, 90. <http://dx.doi.org/10.1016/j.saa.2013.11.059>
  • Ganji Masoud Darvish, Nashtahosseini Mahnaz, Yeganegi Saeed, Rezvani Mahyar: First-principles vdW-DF investigation on the interaction between the oxazepam molecule and C60 fullerene. J Mol Model 2013, 19, 1929. <http://dx.doi.org/10.1007/s00894-013-1758-3>
  • Mukherjee Sibayan, Bauri Ajay K., Bhattacharya Sumanta: Spectroscopic and Theoretical Insights on Non-covalent Binding of PyC60 with a Designed Diporphyrin in Solution. J Solution Chem 2013, 42, 111. <http://dx.doi.org/10.1007/s10953-012-9948-7>
  • Mukherjee Sibayan, Bauri Ajoy K., Bhattacharya Sumanta: Spectroscopic and theoretical insights on effective and selective non-covalent binding between fullerenes (C60 and C70) and a designed diporphyrin in solution. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2013, 115, 835. <http://dx.doi.org/10.1016/j.saa.2013.06.113>
  • Natali Mirco, Ravaglia Marcella, Scandola Franco, Boixel Julien, Pellegrin Yann, Blart Errol, Odobel Fabrice: Long-Range Charge Separation in a Ferrocene–(Zinc Porphyrin)–Naphthalenediimide Triad. Asymmetric Role of 1,2,3-Triazole Linkers. J. Phys. Chem. C 2013, 130912075807001. <http://dx.doi.org/10.1021/jp406405k>
  • Schubert C., Rudolf M., Guldi D. M., Takano Y., Mizorogi N., Herranz M. A., Martin N., Nagase S., Akasaka T.: Rates and energetics of intramolecular electron transfer processes in conjugated metallofullerenes. Philosophical Transactions of the Royal Society A: Mathematical, Physical and Engineering Sciences 2013, 371, 20120490. <http://dx.doi.org/10.1098/rsta.2012.0490>
  • Rudolf Marc, Wolfrum Silke, Guldi Dirk M., Feng Lai, Tsuchiya Takahiro, Akasaka Takeshi, Echegoyen Luis: Endohedral Metallofullerenes-Filled Fullerene Derivatives towards Multifunctional Reaction Center Mimics. Chemistry A European Journal 2012, 18, 5136. <http://dx.doi.org/10.1002/chem.201102844>
  • Krokos Evangelos, Spänig Fabian, Ruppert Michaela, Hirsch Andreas, Guldi Dirk. M.: A Charge-Transfer Challenge: Combining Fullerenes and Metalloporphyrins in Aqueous Environments. Chemistry A European Journal 2012, 18, 1328. <http://dx.doi.org/10.1002/chem.201102851>
  • Mukherjee Partha, Chattopadhyay Subrata, Bhattacharya Sumanta: Spectroscopic and Theoretical Investigations on Supramolecular Interaction of a Newly Designed Monoporphyrin with Fullerenes and Functionalized Fullerenes in Solution. J Solution Chem 2012, 41, 200. <http://dx.doi.org/10.1007/s10953-011-9786-z>
  • Halder Amal, Nayak Sandip K., Chattopadhyay Subrata, Bhattacharya Sumanta: A Rational Approach Towards Determination of Optical Ionicity and Non-covalent Interactions in Fullerene-Calix[4]arene Host-Guest Complexes. J Solution Chem 2012, 41, 223. <http://dx.doi.org/10.1007/s10953-012-9794-7>
  • Mukherjee Partha, Bhattacharya Sumanta: Spectroscopic and theoretical insights on fullerene–octaethylporphyrin self assembled non-covalent conjugates studied in solution. Spectochim Acta A 2012, 90, 186. <http://dx.doi.org/10.1016/j.saa.2012.01.031>
  • Halder Amal, Kundu Kshama, Nayak Sandip K., Chattopadhyay Subrata, Bhattacharya Sumanta: Absorption spectrophotometric, NMR and theoretical investigations on ground state non-covalent interaction of C60 and C70 with a designed trihomocalix[6]arene in solution. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2012, 93, 384. <http://dx.doi.org/10.1016/j.saa.2012.01.079>
  • Halder Amal, Bhattacharya Sumanta: Spectroscopic and quantum chemical investigation on non-covalent interaction in chromophore appended fullerene complexes of calix[4]arene. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2012, 99, 335. <http://dx.doi.org/10.1016/j.saa.2012.08.038>
  • Ray Anamika, Santhosh Kotni, Bhattacharya Sumanta: Photophysical and Theoretical Insights on Fullerene/Zincphthalocyanine Supramolecular Interaction in Solution. J. Phys. Chem. B 2012, 116, 11979. <http://dx.doi.org/10.1021/jp3052483>
  • Grimm Bruno, Jiménez Angel J., Gunderson Victoria L., Vagnini Michael T., Krick Calderon Sandra, Rodríguez-Morgade M. Salomé, Wasielewski Michael R., Guldi Dirk M., Torres Tomás: Synthesis, Characterization, and Photoinduced Energy and Electron Transfer in a Supramolecular Tetrakis (Ruthenium(II) Phthalocyanine) Perylenediimide Pentad. Chem Eur J 2011, 17, 5024. <http://dx.doi.org/10.1002/chem.201002963>
  • Kanematsu Masanori, Naumov Panče, Kojima Takahiko, Fukuzumi Shunichi: Intermolecular and Intracomplex Photoinduced Electron Transfer from Planar and Nonplanar Metalloporphyrins to p-Quinones. Chemistry A European Journal 2011, 17, 12372. <http://dx.doi.org/10.1002/chem.201100493>
  • Habermeyer Benoit, Takai  Atsuro, Gros Claude P., El Ojaimi  Maya, Barbe Jean-Michel, Fukuzumi  Shunichi: Dynamics of Closure of Zinc Bis-Porphyrin Molecular Tweezers with Copper(II) Ions and Electron Transfer. Chemistry A European Journal 2011, 17, 10670. <http://dx.doi.org/10.1002/chem.201101272>
  • Möbius Klaus, Lubitz Wolfgang, Savitsky Anton: Photo-Induced Electron Spin Polarization in Chemical and Biological Reactions: Probing Structure and Dynamics of Transient Intermediates by Multifrequency EPR Spectroscopy. Appl Magn Reson 2011, 41, 113. <http://dx.doi.org/10.1007/s00723-011-0284-7>
  • Halder Amal, Nayak Sandip K., Bhat Suchitra, Chattopadhyay Subrata, Bhattacharya Sumanta: Absorption Spectrophotometric, NMR and Quantum Chemical Investigations of Ground State Non-Covalent Interactions between Fullerenes and a Designed Trihomocalix[6]arene in Solution. J Solution Chem 2011, 40, 929. <http://dx.doi.org/10.1007/s10953-011-9695-1>
  • Mukherjee Sibayan, Banerjee Shrabanti, Bauri Ajay K., Bhattacharya Sumanta: Synthesis, photophysical investigations and molecular structure of the supramolecular complexes of a newly designed diporphyrin receptor with fullerenes C60 and C70 in solution. J Mol Structure 2011, 1004, 13. <http://dx.doi.org/10.1016/j.molstruc.2011.06.039>
  • Pal Debabrata, Bhattacharya Sumanta: Absorption spectrophotometric, fluorescence and theoretical investigations on supramolecular interaction of a designed bisporphyrin with C60 and C70. Spectrochim Acta A Mol Biomol Spectrosc 2011, 79, 638. <http://dx.doi.org/10.1016/j.saa.2011.03.050>
  • Mukherjee Sibayan, Bauri Ajay K., Bhattacharya Sumanta: Determination of binding strength for the supramolecular complexation of a designed bisporphyrin with C60, C70 and their derivatives employing absorption spectrophotometric, fluorescence and quantum chemical calculations. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2011, 79, 1952. <http://dx.doi.org/10.1016/j.saa.2011.05.099>
  • Singh Rachana, Goswami Thakohari: Photophysical and optical limiting properties of multifunctional hemi-ortho ester derivatives of fullerenol: Effects of TBAH doping, fullerenol concentration and solvent polarity. Synthetic Metal 2011, 161, 670. <http://dx.doi.org/10.1016/j.synthmet.2011.01.012>
  • Haillot D., Bauer T., Kröner U., Tamme R., Singh Rachana, Goswami Thakohari: Thermal analysis of phase change materials in the temperature range 120–150°C. Thermochimica Acta 2011, 513, 49. <http://dx.doi.org/10.1016/j.tca.2010.11.012>
  • Ray Anamika, Santhosh Kotni, Bhattacharya Sumanta: New Photophysical Insights in Noncovalent Interaction between Fulleropyrrolidine and a Series of Zincphthalocyanines. J Phys Chem A 2011, 115, 9929. <http://dx.doi.org/10.1021/jp204924z>
  • Zhou Cuisong, Liu Qiaolin, Xu Wei, Wang Chunru, Fang Xiaohong: A water-soluble C60-porphyrin compound for highly efficient DNA photocleavage. Chem Commun 2011, 47, 2982. <http://dx.doi.org/10.1039/c0cc04919k>
  • Lyons Dani M., Mohanraj John, Accorsi Gianluca, Armaroli Nicola, Boyd Peter D. W.: A supramolecular porphyrin–ferrocene–fullerene triad. New J Chem 2011, 35, 632. <http://dx.doi.org/10.1039/c0nj00825g>
  • Iengo Elisabetta, Pantoş G. Dan, Sanders Jeremy K. M., Orlandi Michele, Chiorboli Claudio, Fracasso Sandro, Scandola Franco: A fully self-assembled non-symmetric triad for photoinduced charge separation. Chem Sci 2011, 2, 676. <http://dx.doi.org/10.1039/c0sc00520g>
  • Boixel Julien, Blart Errol, Pellegrin Yann, Odobel Fabrice, Perin Nicola, Chiorboli Claudio, Fracasso Sandro, Ravaglia Marcella, Scandola Franco: Hole-Transfer Dyads and Triads Based on Perylene Monoimide, Quaterthiophene, and Extended Tetrathiafulvalene. Chem Eur J 2010, 16, 9140. <http://dx.doi.org/10.1002/chem.201000640>
  • Mukherjee Sibayan, Bauri Ajoy K., Bhattacharya Sumanta: Photophysical investigations and binding strength in supramolecular interaction of a newly designed diporphyrin tweezer with fullerenes C60 and C70 in solution. chem phys letts 2010, 500, 128. <http://dx.doi.org/10.1016/j.cplett.2010.09.067>
  • Chaudhuri Tandrima, Nath Sukhendu, Chattopadhyay Subrata, Banerjee Manas, Nayak Sandip K.: Supramolecular interactions of meso-tetra-2-chlorophenylporphyrin with fullerenes: A luminescence study. J of Lumin 2010, 130, 507. <http://dx.doi.org/10.1016/j.jlumin.2009.10.022>
  • Sandanayaka Atula S.D., Sasabe Hisahiro, Takata Toshikazu, Ito Osamu: Photoinduced electron transfer processes of fullerene rotaxanes containing various electron-donors. J Photochem Photobiol C Photochem Rev 2010, 11, 73. <http://dx.doi.org/10.1016/j.jphotochemrev.2010.05.001>
  • Wessendorf Florian, Grimm Bruno, Guldi Dirk M., Hirsch Andreas: Pairing Fullerenes and Porphyrins: Supramolecular Wires That Exhibit Charge Transfer Activity. J Am Chem Soc 2010, 132, 10786. <http://dx.doi.org/10.1021/ja101937w>
  • Vivo Paola, Ojala Mikko, Chukharev Vladimir, Efimov Alexander, Lemmetyinen Helge: Role of a phthalocyanine–fullerene dyad in multilayered organic solar cells. J Photochem Photobiol A Chem 2009, 203, 125. <http://dx.doi.org/10.1016/j.jphotochem.2008.12.030>
  • Caporossi Francesco, Floris Barbara, Galloni Pierluca, Gatto Emanuela, Venanzi Mariano, Mozzi Alessia Francesca, Urbani Andrea, Kadish Karl M.: Fluorene–fullerene dyads: Modulation of interaction. Synthetic Metal 2009, 159, 1403. <http://dx.doi.org/10.1016/j.synthmet.2009.03.023>
  • Wang Kui, Wu Yi-Shi, Wang Gui-Tao, Wang Ren-Xiao, Jiang Xi-Kui, Fu Hong-Bing, Li Zhan-Ting: Hydrogen bonding-mediated foldamer-bridged zinc porphyrin-C60 dyads: ideal face-to-face orientation and tunable donor–acceptor interacion. Tetrahedron 2009, 65, 7718. <http://dx.doi.org/10.1016/j.tet.2009.06.087>
  • Molina-Ontoria Agustín, Fernández Gustavo, Wielopolski Mateusz, Atienza Carmen, Sánchez Luis, Gouloumis Andreas, Clark Timothy, Martín Nazario, Guldi Dirk M.: Self-Association and Electron Transfer in Donor−Acceptor Dyads Connected by meta-Substituted Oligomers. J Am Chem Soc 2009, 131, 12218. <http://dx.doi.org/10.1021/ja9024269>
  • Suijkerbuijk Bart M. J. M., Klein Gebbink Robertus J. M.: Porphyrine mit metallorganischen Gruppen: Synthese und Anwendungen. Angew Chem 2008, 120, 7506. <http://dx.doi.org/10.1002/ange.200703362>
  • Suijkerbuijk Bart M. J. M., Klein Gebbink Robertus J. M.: Merging Porphyrins with Organometallics: Synthesis and Applications. Angew Chem Int Ed 2008, 47, 7396. <http://dx.doi.org/10.1002/anie.200703362>
  • Matsuo Yutaka, Matsuo Keiko, Nanao Takeshi, Marczak Renata, Gayathri S. Shankara, Guldi Dirk M., Nakamura Eiichi: A Ruthenium Bridge in Fullerene–Ferrocene Arrays: Synthesis of [Ru(C60Me5)R(CO)2] (R=C6H4Fc, C≡CFc) and Their Charge-Transfer Properties. Chem Asian J 2008, 3, 841. <http://dx.doi.org/10.1002/asia.200700379>
  • González-Rodríguez David, Torres Tomás, Herranz María Ángeles, Echegoyen Luis, Carbonell Esther, Guldi Dirk M.: Screening Electronic Communication through ortho-, meta- and para-Substituted Linkers Separating Subphthalocyanines and C60. Chem Eur J 2008, 14, 7670. <http://dx.doi.org/10.1002/chem.200800910>
  • Huang Sheng-Tung, Ho Chia-Shin, Lin Chun-Mao, Fang Hsu-Wei, Peng Yi-Xiang: Development and biological evaluation of C60 fulleropyrrolidine-thalidomide dyad as a new anti-inflammation agent. biorg med chem 2008, 16, 8619. <http://dx.doi.org/10.1016/j.bmc.2008.08.004>
  • Huang Sheng-Tung, Liao Jian-Sheng, Fang Hsu-Wei, Lin Chun-Mao: Synthesis and anti-inflammation evaluation of new C60 fulleropyrrolidines bearing biologically active xanthine. Biorg Med Chem Lett 2008, 18, 99. <http://dx.doi.org/10.1016/j.bmcl.2007.11.004>
  • Zakharova I. B., Donenko E. A., Biryulin Yu. F., Sharonova L. V., Makarova T. L.: Optical and Vibrational Properties of Thin Film Fullerene‐Zn(II) Tetraphenylporphyrin Complexes. Fullerene Nanot Carbon Nanostruct 2008, 16, 424. <http://dx.doi.org/10.1080/15363830802281898>
  • Kvyatkovskii O. E., Donenko E. G., Zakharova I. B.: Electronic Structure and Optical Properties of Charge‐transfer Fullerene‐porphyrin Complexes: ab initio Calculations. Fullerene Nanot Carbon Nanostruct 2008, 16, 530. <http://dx.doi.org/10.1080/15363830802286160>
  • Ghirotti M., Chiorboli C., Indelli M.T., Scandola F., Casanova M., Iengo E., Alessio E.: Energy transfer pathways in pyridylporphyrin Re(I) adducts. Inorg Chim Ada 2007, 360, 1121. <http://dx.doi.org/10.1016/j.ica.2006.08.039>
  • Murakami Hiroto, Nakanishi Takashi, Morita Makoto, Taniguchi Naoya, Nakashima Naotoshi: Self-Assembled Aggregates and Molecular Bilayer Films of a Double-Chain Fullerene Lipid: Structure and Electrochemistry. Chem Asian J 2006, 1, 860. <http://dx.doi.org/10.1002/asia.200600229>
  • Zhou Zhiguo, Sarova Ginka H., Zhang Sheng, Ou Zhongping, Tat Fatma T., Kadish Karl M., Echegoyen Luis, Guldi Dirk M., Schuster David I., Wilson Stephen R.: Fullerene Polypyridine Ligands: Synthesis, Ruthenium Complexes, and Electrochemical and Photophysical Properties. Chem Eur J 2006, 12, 4241. <http://dx.doi.org/10.1002/chem.200600021>
  • Prodi Anna, Chiorboli Claudio, Scandola Franco, Iengo Elisabetta, Alessio Enzo: Electronic Energy Transfer in a Multiporphyrin-Based Molecular Box. Chem Eur J of Chem Phys 2006, 7, 1514. <http://dx.doi.org/10.1002/cphc.200600065>
  • Tomé João P. C., Pereira Ana M. V. M., Alonso Cristina M. A., Neves Maria G. P. M. S., Tomé Augusto C., Silva Artur M. S., Cavaleiro José A. S., Martínez-Díaz M. Victoria, Torres Tomás, Rahman G. M. Aminur: Synthesis and Photophysical Studies of New Porphyrin-Phthalocyanine Dyads with Hindered Rotation. Eur J Org Chem 2006, 2006, 257. <http://dx.doi.org/10.1002/ejoc.200500558>
  • Savitsky Anton, Möbius Klaus: Photochemical Reactions and Photoinduced Electron-Transfer Processes in Liquids, Frozen Solutions, and Proteins as Studied by Multifrequency Time-Resolved EPR Spectroscopy. HCA 2006, 89, 2544. <http://dx.doi.org/10.1002/hlca.200690232>
  • Valentin M., Bisol A., Agostini G., Giacometti G., Carbonera D.: EPR-detected photoinduced electron transfer in three structurally related molecular triads. Appl Magn Reson 2006, 30, 555. <http://dx.doi.org/10.1007/BF03166218>
  • Scandola Franco, Chiorboli Claudio, Prodi Anna, Iengo Elisabetta, Alessio Enzo: Photophysical properties of metal-mediated assemblies of porphyrins. Coord Chem Rev - 2006, 250, 1471. <http://dx.doi.org/10.1016/j.ccr.2006.01.019>
  • D'Souza Francis, El-Khouly Mohamed E., Gadde Suresh, Zandler Melvin E., McCarty Amy Lea, Araki Yasuyaki, Ito Osamu: Supramolecular triads bearing porphyrin and fullerene via ‘two-point’ binding involving coordination and hydrogen bonding. Tetrahedron 2006, 62, 1967. <http://dx.doi.org/10.1016/j.tet.2005.05.112>
  • Schuster David I., MacMahon Shaun, Guldi Dirk M., Echegoyen Luis, Braslavsky Silvia E.: Synthesis and photophysics of porphyrin–fullerene donor–acceptor dyads with conformationally flexible linkers. Tetrahedron 2006, 62, 1928. <http://dx.doi.org/10.1016/j.tet.2005.07.127>
  • Sánchez Luis, Martín Nazario, González-Cantalapiedra Esther, Echavarren Antonio M., Aminur Rahman G. M., Guldi Dirk M.: Molecular Panels for Energy Transduction in C60-Based Conjugates. Org Lett 2006, 8, 2451. <http://dx.doi.org/10.1021/ol060515g>
  • Guldi Dirk M., Rahman G. M. Aminur, Sgobba Vito, Ehli Christian: Multifunctional molecular carbon materials—from fullerenes to carbon nanotubes. Chem Soc Rev 2006, 35, 471. <http://dx.doi.org/10.1039/b511541h>
  • Benniston Andrew C., Harriman Anthony, Pariani Consuelo, Sams Craig A.: Intramolecular energy-transfer processes in a bis(porphyrin)-ruthenium(ii) bis(2,2?:6?,2?-terpyridine) molecular array. Phys Chem Chem Phys 2006, 8, 2051. <http://dx.doi.org/10.1039/b600420b>
  • Di Valentin M., Bisol A., Agostini G., Moore A. L., Moore T. A., Gust D., Palacios R. E., Gould S. L., Carbonera D.: Time-resolved EPR investigation of charge recombination to a triplet state in a carotene-diporphyrin triad. Mole Phys 2006, 104, 1595. <http://dx.doi.org/10.1080/00268970600638572>
  • Hauke Frank, Hirsch Andreas, Atalick Stefan, Guldi Dirk: Quantitative Transduction of Excited-State Energy inFluorophore-Heterofullerene Conjugates. Eur J Org Chem 2005, 2005, 1741. <http://dx.doi.org/10.1002/ejoc.200400771>
  • Thomas K. George, George Manapurathu V., Kamat Prashant V.: Photoinduced Electron-Transfer Processes in Fullerene-Based Donor-Acceptor Systems. HCA 2005, 88, 1291. <http://dx.doi.org/10.1002/hlca.200590106>
  • Litvinov Aleksey L., Konarev Dmitri V., Kovalevsky Andrey Yu., Neretin Ivan S., Coppens Philip, Lyubovskaya Rimma N.: [60]Fullerene Complexes with Supramolecular Zinc Tetraphenylporphyrin Assemblies:  Synthesis, Crystal Structures, and Optical Properties. Growth Des 2005, 5, 1807. <http://dx.doi.org/10.1021/cg050095m>
  • Kieran Amy L., Pascu Sofia I., Jarrosson Thibaut, Sanders Jeremy K. M.: Inclusion of C60 into an adjustable porphyrin dimer generated by dynamic disulfide chemistry. Chem Commun 2005, 1276. <http://dx.doi.org/10.1039/b417951j>
  • Maes Mio, Sasabe Hisahiro, Kihara Nobuhiro, Araki Yasuyuki, Furusho Yoshio, Mizuno Kazuhiko, Takata Toshikazu, Ito Osamu: Photoinduced electron and energy transfer processes in rotaxanes containing zinc porphyrin as pendant and [60]fullerene and ferrocene as axle ends. J. Porphyrins Phthalocyanines 2005, 09, 724. <http://dx.doi.org/10.1142/S1088424605000836>
  • Konarev Dmitri V., Litvinov Alexey L., Neretin Ivan S., Drichko Natalia V., Slovokhotov Yury L., Lyubovskaya Rimma N., Howard Judith A. K., Yufit D. S.: Formation of Coordination Porphyrin Pentamers in New Supramolecular Complex of Fullerene:  {(ZnTPP)4·4-TPyP}·(C60)2·(C6H5CN)3.5. Growth Des 2004, 4, 643. <http://dx.doi.org/10.1021/cg034259f>
  • Padmawar Prashant A., Canteenwala Taizoon, Verma Sarika, Tan Loon‐Seng, Chiang Long Y.: Synthesis and Photophysical Properties of C60‐Diphenylaminofluorene Dyad and Multiads. Journal of Macromolecular Science, Part A 2004, 41, 1387. <http://dx.doi.org/10.1081/MA-200035292>