Electrically conducting porphyrin and porphyrin-fullerene electropolymers
Abstract
Compounds with aryl ring(s) at porphyrin meso position(s) bearing an amino group in position 4 relative to the porphyrin macrocycle, and at least one unsubstituted 5 (hydrogen-bearing) meso position with the 10-, 15-, and/or 20-relationship to the aryl ring bearing the amino group, and metal complexes thereof, feature broad spectral absorption throughout the visible region. These compounds are electropolymerized to form electrically conducting porphyrin and porphyrin-fullerene polymers that are useful in photovoltaic applications. The structure of one such electrically conducting porphyrin polymer is shown below. ##STR00001##
- Inventors:
- Issue Date:
- Research Org.:
- Arizona State University, Scottsdale, AZ, USA
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1126698
- Patent Number(s):
- 8669359
- Application Number:
- 12/552,187
- Assignee:
- Arizona Board of Regents for and on behalf of Arizona State University (Scottsdale, AZ)
- Patent Classifications (CPCs):
-
B - PERFORMING OPERATIONS B82 - NANOTECHNOLOGY B82Y - SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
- DOE Contract Number:
- FG02-03ER15393
- Resource Type:
- Patent
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 36 MATERIALS SCIENCE
Citation Formats
Gust, Jr., John Devens, Liddell, Paul Anthony, Gervaldo, Miguel Andres, Bridgewater, James Ward, Brennan, Bradley James, Moore, Thomas Andrew, and Moore, Ana Lorenzelli. Electrically conducting porphyrin and porphyrin-fullerene electropolymers. United States: N. p., 2014.
Web.
Gust, Jr., John Devens, Liddell, Paul Anthony, Gervaldo, Miguel Andres, Bridgewater, James Ward, Brennan, Bradley James, Moore, Thomas Andrew, & Moore, Ana Lorenzelli. Electrically conducting porphyrin and porphyrin-fullerene electropolymers. United States.
Gust, Jr., John Devens, Liddell, Paul Anthony, Gervaldo, Miguel Andres, Bridgewater, James Ward, Brennan, Bradley James, Moore, Thomas Andrew, and Moore, Ana Lorenzelli. Tue .
"Electrically conducting porphyrin and porphyrin-fullerene electropolymers". United States. https://www.osti.gov/servlets/purl/1126698.
@article{osti_1126698,
title = {Electrically conducting porphyrin and porphyrin-fullerene electropolymers},
author = {Gust, Jr., John Devens and Liddell, Paul Anthony and Gervaldo, Miguel Andres and Bridgewater, James Ward and Brennan, Bradley James and Moore, Thomas Andrew and Moore, Ana Lorenzelli},
abstractNote = {Compounds with aryl ring(s) at porphyrin meso position(s) bearing an amino group in position 4 relative to the porphyrin macrocycle, and at least one unsubstituted 5 (hydrogen-bearing) meso position with the 10-, 15-, and/or 20-relationship to the aryl ring bearing the amino group, and metal complexes thereof, feature broad spectral absorption throughout the visible region. These compounds are electropolymerized to form electrically conducting porphyrin and porphyrin-fullerene polymers that are useful in photovoltaic applications. The structure of one such electrically conducting porphyrin polymer is shown below. ##STR00001##},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Tue Mar 11 00:00:00 EDT 2014},
month = {Tue Mar 11 00:00:00 EDT 2014}
}
Works referenced in this record:
New and Efficient Synthesis of Oligomeric Porphyrins via Stepwise Nucleophilic Substitution of Aminoporphyrins to Cyanuric Chloride
journal, August 1995
- Ichihara, Kanako; Naruta, Yoshinori
- Chemistry Letters, Vol. 24, Issue 8
Photoelectrochemical characterisation of porphyrin-coated electrodes
journal, January 1991
- Basu, J.; Rohatgi-Mukherjee, K. K.
- Solar Energy Materials, Vol. 21, Issue 4, p. 317-325
Electrochemistry of various substituted aminophenyl iron porphyrins: Part I. Redox properties of dissolved, adsorbed and electropolymerized species
journal, July 1989
- Bettelheim, A.; Ozer, D.; Harth, R.
- Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Vol. 266, Issue 1, p. 93-108
Electrocatalysis of dioxygen reduction in aqueous acid and base by multimolecular layer films of electropolymerized cobalt tetra(o-aminophenyl)porphyrin
journal, February 1987
- Bettelheim, A.; White, B. A.; Murray, Royce W.
- Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Vol. 217, Issue 2, p. 271-286
Fullerene−Porphyrin Constructs
journal, April 2005
- Boyd, Peter D. W.; Reed, Christopher A.
- Accounts of Chemical Research, Vol. 38, Issue 4
Electropolymerization of Tetrakis(o-aminophenyl)porphyrin and Relevant Transition Metal Complexes from Aqueous Solution. The Resulting Modified Electrodes as Potentiometric Sensors
journal, June 1999
- Bruti, Enrico Maria; Giannetto, Marco; Mori, Giovanni
- Electroanalysis, Vol. 11, Issue 8, p. 565-572
Synthesis of covalently-linked linear donor-acceptor copolymers containing porphyrins and oligothiophenes
journal, August 2004
- Duanmu, Chuan-Song; Chen, Zhang-Ping; Yu, Xue-Song
- Chinese Journal of Chemistry, Vol. 22, Issue 8
An efficient synthesis of highly functionalized asymmetric porphyrins with organolithium reagents
journal, January 2001
- Feng, Xiangdong; Senge, Mathias O.
- Journal of the Chemical Society, Perkin Transactions 1, Issue 9
Comparative study of electropolymerized cobalt porphyrin and phthalocyanine based films for the electrochemical activation of thiols
journal, January 2002
- Griveau, Sophie; Albin, Valérie; Pauporté, Thierry
- Journal of Materials Chemistry, Vol. 12, Issue 2
A Scalable Synthesis of Meso-Substituted Dipyrromethanes
journal, November 2003
- Laha, Joydev K.; Dhanalekshmi, Savithri; Taniguchi, Masahiko
- Organic Process Research & Development, Vol. 7, Issue 6
Very stable, highly electroactive polymers of zinc(II)-5,15-bisthienylphenyl porphyrin exhibiting charge-trapping effects
journal, June 2005
- Li, Guangtao; Bhosale, Sheshanath; Tao, Shengyang
- Polymer, Vol. 46, Issue 14, p. 5299-5307
Porphyrin-Based Hole Conducting Electropolymer
journal, January 2008
- Liddell, Paul A.; Gervaldo, Miguel; Bridgewater, James W.
- Chemistry of Materials, Vol. 20, Issue 1
Synthesis, electrochemistry, absorption and electro-polymerization of aniline-ethynyl metalloporphyrins
journal, January 2005
- Lin, Ching-Yao; Hung, Yu-Chun; Liu, Chih-Ming
- Dalton Transactions, Issue 2
Oxidative electrochemistry of electropolymerized metalloprotoporphyrin films
journal, March 1984
- Macor, K. A.; Spiro, T. G.
- Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Vol. 163, Issue 1-2, p. 223-236
Conductive polymeric Cu(II) tetrakis(3-methoxy-4-hydroxyphenyl) porphyrin as a photosensitizer in a photoelectrochemical Cell
journal, May 1992
- Malinski, Tadeusz; Ciszewski, Aleksander; Fish, Judith
- Advanced Materials, Vol. 4, Issue 5, p. 354-357
Photovoltaic effects in porphyrin polymer films and heterojunctions
journal, September 1996
- Marée, C. H. M.; Roosendaal, S. J.; Savenije, T. J.
- Journal of Applied Physics, Vol. 80, Issue 6
Anodic oxidation and physicochemical properties of various porphyrin-fluorenes or -spirobifluorenes: Synthesis of new polymers for heterogeneous catalytic reactions
journal, September 2005
- Poriel, Cyril; Ferrand, Yann; Le Maux, Paul
- Journal of Electroanalytical Chemistry, Vol. 583, Issue 1, p. 92-103
Polarized Infrared Spectra of Photooriented Matrix-Isolated Free-Base Porphyrin Isotopomers
journal, September 1995
- Radziszewski, Juliusz G.; Nepras, Milos; Balaji, V.
- The Journal of Physical Chemistry, Vol. 99, Issue 39, p. 14254-14260
Hole transport in porphyrin thin films
journal, August 2001
- Savenije, Tom J.; Goossens, Albert
- Physical Review B, Vol. 64, Issue 11
Energy and Electron Transfer in Polyacetylene-Linked Zinc-Porphyrin-[60]Fullerene Molecular Wires
journal, May 2005
- Vail, Sean A.; Krawczuk, Paul J.; Guldi, Dirk M.
- Chemistry - A European Journal, Vol. 11, Issue 11
Electroactive porphyrin films from electropolymerized metallotetra(o-aminophenyl)porphyrins
journal, July 1985
- White, B. A.; Murray, Royce W.
- Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, Vol. 189, Issue 2, p. 345-352
Lead structures for applications in photodynamic therapy. Part 1: Synthesis and variation of m-THPC (Temoporfin) related amphiphilic A2BC-type porphyrins
journal, June 2005
- Wiehe, Arno; Shaker, Yasser M.; Brandt, Johan C.
- Tetrahedron, Vol. 61, Issue 23, p. 5535-5564
Porphyrins, phthalocyanines and related systems in polymer phases
journal, June 2000
- Wohrle, Dieter
- Journal of Porphyrins and Phthalocyanines (JPP), Vol. 04, Issue 04, p. 418-424
Excited-State Energy-Transfer Dynamics in Self-Assembled Triads Composed of Two Porphyrins and an Intervening Bis(dipyrrinato)metal Complex
journal, October 2003
- Yu, Lianhe; Muthukumaran, Kannan; Sazanovich, Igor V.
- Inorganic Chemistry, Vol. 42, Issue 21
DFT study on the influence of meso-phenyl substitution on the geometric, electronic structure and vibrational spectra of free base porphyrin
journal, August 2005
- Zhang, Ying-Hui; Ruan, Wen-Juan; Li, Zhi-Yun
- Chemical Physics, Vol. 315, Issue 1-2, p. 201-213