Search Menu
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information
Search Scholarly Publications

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

Abstract

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.

Authors:
 [1];  [1];  [1];  [1]
+ Show Author Affiliations
  1. Arizona State University, Tempe, AZ (United States)
Publication Date:
Research Org.:
Arizona State Univ., Tempe, AZ (United States)
Sponsoring Org.:
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
OSTI Identifier:
1429466
Alternate Identifier(s):
OSTI ID: 1359016
Grant/Contract Number:  
FG02-03ER15393; SC0001016
Resource Type:
Accepted Manuscript
Journal Name:
Dyes and Pigments
Additional Journal Information:
Journal Volume: 136; Journal Issue: C; Journal ID: ISSN 0143-7208
Publisher:
Elsevier
Country of Publication:
United States
Language:
English
Subject:
14 SOLAR ENERGY; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; dye-sensitized solar cells; panchromatic; BODIPY; porphyrin; scaffold

Citation Formats

Watson, Brian L., Moore, Thomas A., Moore, Ana L., and Gust, Devens. Synthesis of a novel building block for the preparation of multi-chromophoric sensitizers for panchromatic dye-sensitized solar cells. United States: N. p., 2016. Web. doi:10.1016/j.dyepig.2016.09.037.
Copy to clipboard
Watson, Brian L., Moore, Thomas A., Moore, Ana L., & Gust, Devens. Synthesis of a novel building block for the preparation of multi-chromophoric sensitizers for panchromatic dye-sensitized solar cells. United States. https://doi.org/10.1016/j.dyepig.2016.09.037
Copy to clipboard
Watson, Brian L., Moore, Thomas A., Moore, Ana L., and Gust, Devens. Fri . "Synthesis of a novel building block for the preparation of multi-chromophoric sensitizers for panchromatic dye-sensitized solar cells". United States. https://doi.org/10.1016/j.dyepig.2016.09.037. https://www.osti.gov/servlets/purl/1429466.
Copy to clipboard
@article{osti_1429466,
title = {Synthesis of a novel building block for the preparation of multi-chromophoric sensitizers for panchromatic dye-sensitized solar cells},
author = {Watson, Brian L. and Moore, Thomas A. and Moore, Ana L. and Gust, Devens},
abstractNote = {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.},
doi = {10.1016/j.dyepig.2016.09.037},
journal = {Dyes and Pigments},
number = C,
volume = 136,
place = {United States},
year = {Fri Sep 23 00:00:00 EDT 2016},
month = {Fri Sep 23 00:00:00 EDT 2016}
}
Copy to clipboard
Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1016/j.dyepig.2016.09.037
Copyright Statement
Other availability
Search WorldCat Search WorldCat to find libraries that may hold this journal
Citation Metrics:
Cited by: 14 works
Citation information provided by
Web of Science
Save / Share:
Export Metadata
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.

Works referenced in this record:

Influence of the Anchoring Modes on the Electronic and Photovoltaic Properties of D−π–A Dyes
journal, August 2012

  • Katono, Masataka; Bessho, Takeru; Wielopolski, Mateusz
  • The Journal of Physical Chemistry C, Vol. 116, Issue 32
  • DOI: 10.1021/jp304490a

What Is the Best Anchoring Group for a Dye in a Dye-Sensitized Solar Cell?
journal, May 2012

  • Ambrosio, Francesco; Martsinovich, Natalia; Troisi, Alessandro
  • The Journal of Physical Chemistry Letters, Vol. 3, Issue 11
  • DOI: 10.1021/jz300520p

Optimizing Dyes for Dye-Sensitized Solar Cells
journal, April 2006

Dye-Sensitized Solar Cells
journal, November 2010

  • Hagfeldt, Anders; Boschloo, Gerrit; Sun, Licheng
  • Chemical Reviews, Vol. 110, Issue 11
  • DOI: 10.1021/cr900356p

Dye-sensitized solar cells
journal, October 2003

  • Grätzel, Michael
  • Journal of Photochemistry and Photobiology C: Photochemistry Reviews, Vol. 4, Issue 2, p. 145-153
  • DOI: 10.1016/S1389-5567(03)00026-1

Enhanced dye-sensitized solar cell photocurrent and efficiency using a Y-shaped, pyrazine-containing heteroaromatic sensitizer linkage
journal, January 2015

  • Watson, Brian L.; Sherman, Benjamin D.; Moore, Ana L.
  • Physical Chemistry Chemical Physics, Vol. 17, Issue 24
  • DOI: 10.1039/C5CP00860C

Ladder polyquinoxalines
journal, September 1966

  • Stille, J. K.; Mainen, E. L.
  • Journal of Polymer Science Part B: Polymer Letters, Vol. 4, Issue 9
  • DOI: 10.1002/pol.1966.110040916

Hexaazatriphenylene (HAT) versus tri-HAT: The Bigger the Better?
journal, August 2011

  • Juárez, Rafael; Oliva, María Moreno; Ramos, Mar
  • Chemistry - A European Journal, Vol. 17, Issue 37
  • DOI: 10.1002/chem.201101198

On the Homoconjugation of Two Acceptor Groups
journal, August 1998

Cavitand−Porphyrins
journal, May 2001

  • Starnes, Stephen D.; Rudkevich, Dmitry M.; Rebek, Julius
  • Journal of the American Chemical Society, Vol. 123, Issue 20
  • DOI: 10.1021/ja010038r

Preparation, Characterization, and FET Properties of Novel Dicyanopyrazinoquinoxaline Derivatives
journal, May 2004

  • Nishida, Jun-ichi; Murai, Shio
  • Organic Letters, Vol. 6, Issue 12, p. 2007-2010
  • DOI: 10.1021/ol0494010

Recent Developments in the Synthesis of Quinoxaline Derivatives by Green Synthetic Approaches
journal, January 2013

  • Nageswar, Y. V. D.; Reddy, K. Harsha Vardhan; Ramesh, K.
  • Organic Preparations and Procedures International, Vol. 45, Issue 1
  • DOI: 10.1080/00304948.2013.743419

Pyrazine-Containing Acene-Type Molecular Ribbons with up to 16 Rectilinearly Arranged Fused Aromatic Rings
journal, July 2008

  • Gao, Baoxiang; Wang, Ming; Cheng, Yanxiang
  • Journal of the American Chemical Society, Vol. 130, Issue 26
  • DOI: 10.1021/ja800311a

Efficient Synthesis of 1,4,5,12-Tetraazatriphenylene and Derivatives
journal, October 2004

  • Abeywickrama, Chandima; Baker, Arthur David
  • The Journal of Organic Chemistry, Vol. 69, Issue 22
  • DOI: 10.1021/jo0495283

Synthesis and characterization of thermally stable polymers containing phenazine
journal, March 2000

New photosensitizers containing the dipyridoquinoxaline moiety and their use in dye-sensitized solar cells
journal, November 2015

Building Blocks for Self-Assembled Porphyrinic Photonic Wires
journal, March 2005

  • Koepf, M.; Trabolsi, A.; Elhabiri, M.
  • Organic Letters, Vol. 7, Issue 7
  • DOI: 10.1021/ol050033p

Porphyrin-Sensitized Solar Cells with Cobalt (II/III)-Based Redox Electrolyte Exceed 12 Percent Efficiency
journal, November 2011

Electrochemistry and Electrogenerated Chemiluminescence of BODIPY Dyes
journal, March 2012

  • Nepomnyashchii, Alexander B.; Bard, Allen J.
  • Accounts of Chemical Research, Vol. 45, Issue 11
  • DOI: 10.1021/ar200278b

Multiantenna Artificial Photosynthetic Reaction Center Complex
journal, May 2009

  • Terazono, Yuichi; Kodis, Gerdenis; Liddell, Paul A.
  • The Journal of Physical Chemistry B, Vol. 113, Issue 20
  • DOI: 10.1021/jp900835s
    Sort by:
    [ × clear filter / sort ]

    Works referencing / citing this record:

      Sort by:
      [ × clear filter / sort ]

      Similar Records in DOE PAGES and OSTI.GOV collections: