Synthesis of new donor-acceptor polymers containing thiadiazoloquinoxaline and pyrazinoquinoxaline moieties: Low-band gap, high optical contrast, and almost black colored materials

Elif Kose Unver, Simge Tarkuc, Derya Baran, Cihangir Tanyeli, Levent Toppare*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

Two low band gap conjugated polymers, poly[4,9-bis(4-hexylthien-2-yl)-6,7- di(thien-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline] (PHTTQ) and poly[5,10-bis(4-hexylthien-2-yl)-2,3,7,8-tetra(thien-2-yl)pyrazino[2,3-g] quinoxaline] (PHTPQ), consisting of alternating electron-rich 3-hexylthiophene and electron-deficient 6,7-di(thien-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline (TTQ) and 2,3,7,8-tetra(thien-2-yl)-2,3-dihydropyrazino[2,3-g]quinoxaline (TPQ) units were synthesized electrochemically. The structures of the π-conjugated monomers were tailored using thiophene as the pendant group on the acceptor units (TTQ and TPQ). The electrochemical and optical properties of the polymers were investigated by cyclic voltammetry and UV-vis-NIR spectroscopy. The absorption spectra of PHTPQ, revealing a 1.0 eV band gap, exhibited three maxima at 352 nm, 535 nm, and 750 nm. Consequently, its absorption spectra cover the region between 400 and 800 nm, which make the polymer almost black in appearance. PHTTQ shows a λ max value of 820 nm and a band gap of 0.8 eV which is very low among other [1,2,5]thiadiazolo[3,4-g]quinoxaline- containing donor-acceptor type polymers.

Original languageEnglish (US)
Pages (from-to)2725-2729
Number of pages5
JournalTetrahedron Letters
Volume52
Issue number21
DOIs
StatePublished - May 25 2011

Keywords

  • Donor-acceptor polymers
  • Low-band gap polymers
  • Pyrazinoquinoxaline
  • Thiadiazoloquinoxaline

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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