Conformational analysis and electronic properties of 2-cyano-3-(thiophen-2-yl)acrylic acid in sensitizers for dye-sensitized solar cells: A theoretical study

Mannix P. Balanay, Se Mi Kim, Mi Jung Lee, Sang Hee Lee, Dong Hee Kim

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

The conformational and electronic properties of 2-cyano-3-(thiophen-2-yl)acrylic acid (TCA) in analogues used as sensitizers in dye-sensitized solar cells was examined using density functional theory (DFT) and natural bond orbital analysis methods. A relaxed potential energy surface scan was performed on NKX-2677 by rotating the C-C bond between the thiophene and cyanoacrylic acid which yielded activation energy barriers of about 13 kcal/mol for both E and Z configurations. The most stable conformation of all the analogues was E-180 except for NKX-2587 which has an electrostatic repulsion between the oxygen of the coumarin and the nitrogen of the cyanoacrylic acid. The increase in the electron delocalization between the thiophene and cyanoacrylic acid influences the stability for most of the analogues. But for NKX-2600, even though there was a greater deviation from the planarity of TCA, the stability was mainly due to the presence of a weak hydrogen bond between the hydrogen of the methyl group of the amine located in the donor moiety and the nitrogen of the cyanoacrylic acid. The vertical excitation energies of the analogues containing TCA were calculated by time-dependent DFT method. There were slight differences in its vertical excitation energies but the oscillator strengths vary significantly especially in the case of NKX-2600.

Original languageEnglish
Pages (from-to)2077-2082
Number of pages6
JournalBulletin of the Korean Chemical Society
Volume30
Issue number9
DOIs
Publication statusPublished - Sep 2009
Externally publishedYes

Keywords

  • Conformation
  • Cyanoacrylic acid
  • DFT
  • DSSC
  • Thiophene

ASJC Scopus subject areas

  • Chemistry(all)

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