Journal
ACS APPLIED MATERIALS & INTERFACES
Volume 8, Issue 8, Pages 5376-5384Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsami.5b12503
Keywords
thienopyrazine; NIR dyes; C-H activation; dye-sensitized solar cells; proaromaticity; panchromatic absorption
Funding
- NSF CAREER program [NSF-1455167]
- University of Mississippi
- European Community's Seventh Framework Program, NANOMATCELL [ENERGY.2012.10.2.1, 308997]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1455167] Funding Source: National Science Foundation
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Thieno[3,4-b]pyrazine (TPz) is examined as an electron deficient pi-bridge enabling near-infrared (NIR) spectral access in dye sensitized solar cells (DSCs). Seven dissymmetric dyes for DSCs were synthesized (NL2-NL8) with TPz as the pi-bridge utilizing palladium catalyzed C-H activation methodology. C-H bond cross-coupling was uniquely effective among the cross-couplings and electrophilic aromatic substitution reactions analyzed in monofunctionalizing the TPz building block. The TPz-based NL2-NL8 dyes examine the effects of various donors, pi-spacers, and acceptors within the donor-pi bridge-acceptor (D-pi-A) dye design. Proaromatic TPz stabilizes the excited-state oxidation potential (Es+/s*) of the dyes by maintaining aromaticity upon excitation of the dye molecule. This leads to concise conjugated systems capable of accessing the NIR region. Through judicious structural modifications, dye band gaps were reduced to 1.48 eV, and power conversion efficiencies (PCEs) reached 7.1% in this first generation TPz-dye series.
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