Synthesis of a novel building block for the preparation of multi-chromophoric sensitizers for panchromatic dye-sensitized solar cells

Watson, Brian L.; Moore, Thomas A.; Moore, Ana L.; Gust, Devens

doi:10.1016/j.dyepig.2016.09.037

Title: Synthesis of a novel building block for the preparation of multi-chromophoric sensitizers for panchromatic dye-sensitized solar cells

Journal Article · Fri Sep 23 00:00:00 EDT 2016 · Dyes and Pigments

DOI:https://doi.org/10.1016/j.dyepig.2016.09.037· OSTI ID:1429466

Watson, Brian L. ^[1]; Moore, Thomas A. ^[1]; Moore, Ana L. ^[1]; Gust, Devens ^[1]

Arizona State University, Tempe, AZ (United States)

For this study, a simple 3-step synthesis of a novel pyrazine-containing heteroaromatic building block for use as a scaffold for producing multi-chromophoric sensitizers for use in dye sensitized solar cells has been developed. This moiety features two esterified carboxylic acid groups whose hydrolysis provides moieties for anchoring to nanoparticulate metal oxides and two bromine atoms that facilitate attachment of chromophores via palladium mediated cross-coupling methods. The utility of the building block for the synthesis of complex dye motifs is demonstrated by the preparation of a novel panchromatic dye featuring a BODIPY chromophore and a strongly electron donating porphyrin chromophore using both Suzuki and copper-free Sonogashira cross-coupling methods. The building block could be used either to attach two different or identical dye moieties to the metal oxide, or to attach an electron injection dye plus an auxiliary absorber, photoprotective agent, secondary redox moiety, etc.

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Research Organization:: Arizona State Univ., Tempe, AZ (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division

Grant/Contract Number:: FG02-03ER15393; SC0001016

OSTI ID:: 1429466

Alternate ID(s):: OSTI ID: 1359016

Journal Information:: Dyes and Pigments, Vol. 136, Issue C; ISSN 0143-7208

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 14 works

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References (23)

Influence of the Anchoring Modes on the Electronic and Photovoltaic Properties of D−π–A Dyes Katono, Masataka; Bessho, Takeru; Wielopolski, Mateusz The Journal of Physical Chemistry C, Vol. 116, Issue 32 https://doi.org/10.1021/jp304490a	journal	August 2012
What Is the Best Anchoring Group for a Dye in a Dye-Sensitized Solar Cell? Ambrosio, Francesco; Martsinovich, Natalia; Troisi, Alessandro The Journal of Physical Chemistry Letters, Vol. 3, Issue 11 https://doi.org/10.1021/jz300520p	journal	May 2012
Optimizing Dyes for Dye-Sensitized Solar Cells Robertson, Neil Angewandte Chemie International Edition, Vol. 45, Issue 15 https://doi.org/10.1002/anie.200503083	journal	April 2006
Dye-Sensitized Solar Cells Hagfeldt, Anders; Boschloo, Gerrit; Sun, Licheng Chemical Reviews, Vol. 110, Issue 11 https://doi.org/10.1021/cr900356p	journal	November 2010
Dye-sensitized solar cells Grätzel, Michael Journal of Photochemistry and Photobiology C: Photochemistry Reviews, Vol. 4, Issue 2, p. 145-153 https://doi.org/10.1016/S1389-5567(03)00026-1	journal	October 2003
Enhanced dye-sensitized solar cell photocurrent and efficiency using a Y-shaped, pyrazine-containing heteroaromatic sensitizer linkage Watson, Brian L.; Sherman, Benjamin D.; Moore, Ana L. Physical Chemistry Chemical Physics, Vol. 17, Issue 24 https://doi.org/10.1039/C5CP00860C	journal	January 2015
Polystyrene-supported AlCl3 as a highly active and reusable heterogeneous lewis acid catalyst for the one-pot synthesis of quinoxalines Rahmatpour, Ali Heteroatom Chemistry, Vol. 23, Issue 5 https://doi.org/10.1002/hc.21039	journal	January 2012
Ladder polyquinoxalines Stille, J. K.; Mainen, E. L. Journal of Polymer Science Part B: Polymer Letters, Vol. 4, Issue 9 https://doi.org/10.1002/pol.1966.110040916	journal	September 1966
Hexaazatriphenylene (HAT) versus tri-HAT: The Bigger the Better? Juárez, Rafael; Oliva, María Moreno; Ramos, Mar Chemistry - A European Journal, Vol. 17, Issue 37 https://doi.org/10.1002/chem.201101198	journal	August 2011
On the Homoconjugation of Two Acceptor Groups Doerner, Thomas; Gleiter, Rolf; Neugebauer, Franz A. European Journal of Organic Chemistry, Vol. 1998, Issue 8 https://doi.org/10.1002/(SICI)1099-0690(199808)1998:8<1615::AID-EJOC1615>3.0.CO;2-N	journal	August 1998
Cavitand−Porphyrins Starnes, Stephen D.; Rudkevich, Dmitry M.; Rebek, Julius Journal of the American Chemical Society, Vol. 123, Issue 20 https://doi.org/10.1021/ja010038r	journal	May 2001
Dinuclear Ruthenium(II) Polypyridyl Complexes Containing Large, Redox-Active, Aromatic Bridging Ligands: Synthesis, Characterization, and Intramolecular Quenching of MLCT Excited States Kim, Mahn-Jong; Konduri, Rama; Ye, Hongwei Inorganic Chemistry, Vol. 41, Issue 9 https://doi.org/10.1021/ic011028u	journal	May 2002
Preparation, Characterization, and FET Properties of Novel Dicyanopyrazinoquinoxaline Derivatives Nishida, Jun-ichi; Murai, Shio Organic Letters, Vol. 6, Issue 12, p. 2007-2010 https://doi.org/10.1021/ol0494010	journal	May 2004
Recent Developments in the Synthesis of Quinoxaline Derivatives by Green Synthetic Approaches Nageswar, Y. V. D.; Reddy, K. Harsha Vardhan; Ramesh, K. Organic Preparations and Procedures International, Vol. 45, Issue 1 https://doi.org/10.1080/00304948.2013.743419	journal	January 2013
ZrOCl2·8H2O in water: An efficient catalyst for rapid one-pot synthesis of pyridopyrazines, pyrazines and 2,3-disubstituted quinoxalines Bardajee, Ghasem Rezanejade Comptes Rendus Chimie, Vol. 16, Issue 10 https://doi.org/10.1016/j.crci.2013.02.018	journal	October 2013
Pyrazine-Containing Acene-Type Molecular Ribbons with up to 16 Rectilinearly Arranged Fused Aromatic Rings Gao, Baoxiang; Wang, Ming; Cheng, Yanxiang Journal of the American Chemical Society, Vol. 130, Issue 26 https://doi.org/10.1021/ja800311a	journal	July 2008
Efficient Synthesis of 1,4,5,12-Tetraazatriphenylene and Derivatives Abeywickrama, Chandima; Baker, Arthur David The Journal of Organic Chemistry, Vol. 69, Issue 22 https://doi.org/10.1021/jo0495283	journal	October 2004
Synthesis and characterization of thermally stable polymers containing phenazine Gajiwala, H. M.; Zand, R. Polymer, Vol. 41, Issue 6 https://doi.org/10.1016/S0032-3861(99)00371-7	journal	March 2000
New photosensitizers containing the dipyridoquinoxaline moiety and their use in dye-sensitized solar cells Shahroosvand, Hashem; Rezaei, Shiva; Abbaspour, Saeid Journal of Photochemistry and Photobiology B: Biology, Vol. 152 https://doi.org/10.1016/j.jphotobiol.2014.12.011	journal	November 2015
Building Blocks for Self-Assembled Porphyrinic Photonic Wires Koepf, M.; Trabolsi, A.; Elhabiri, M. Organic Letters, Vol. 7, Issue 7 https://doi.org/10.1021/ol050033p	journal	March 2005
Porphyrin-Sensitized Solar Cells with Cobalt (II/III)-Based Redox Electrolyte Exceed 12 Percent Efficiency Yella, A.; Lee, H. -W.; Tsao, H. N. Science, Vol. 334, Issue 6056 https://doi.org/10.1126/science.1209688	journal	November 2011
Electrochemistry and Electrogenerated Chemiluminescence of BODIPY Dyes Nepomnyashchii, Alexander B.; Bard, Allen J. Accounts of Chemical Research, Vol. 45, Issue 11 https://doi.org/10.1021/ar200278b	journal	March 2012
Multiantenna Artificial Photosynthetic Reaction Center Complex Terazono, Yuichi; Kodis, Gerdenis; Liddell, Paul A. The Journal of Physical Chemistry B, Vol. 113, Issue 20 https://doi.org/10.1021/jp900835s	journal	May 2009

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Title: Synthesis of a novel building block for the preparation of multi-chromophoric sensitizers for panchromatic dye-sensitized solar cells

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