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

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Abstract

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.

Original languageEnglish
Pages (from-to)893-897
Number of pages5
JournalDyes and Pigments
Volume136
DOIs
Publication statusPublished - Jan 1 2017

Fingerprint

Coloring Agents
Chromophores
Dyes
Oxides
Metals
Pyrazines
Bromine
Electron injection
Porphyrins
Palladium
Carboxylic Acids
Carboxylic acids
Scaffolds
Copper
Hydrolysis
Atoms
Dye-sensitized solar cells
Electrons

Keywords

  • BODIPY
  • Dye-sensitized solar cells
  • Panchromatic
  • Porphyrin
  • Scaffold

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Process Chemistry and Technology

Cite this

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title = "Synthesis of a novel building block for the preparation of multi-chromophoric sensitizers for panchromatic dye-sensitized solar cells",
abstract = "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.",
keywords = "BODIPY, Dye-sensitized solar cells, Panchromatic, Porphyrin, Scaffold",
author = "Watson, {Brian L.} and Moore, {Thomas A} and Moore, {Ana L} and Gust, {John Devens}",
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AU - Watson, Brian L.

AU - Moore, Thomas A

AU - Moore, Ana L

AU - Gust, John Devens

PY - 2017/1/1

Y1 - 2017/1/1

N2 - 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.

AB - 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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KW - Dye-sensitized solar cells

KW - Panchromatic

KW - Porphyrin

KW - Scaffold

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