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

Date

2011-05-25

Author

Unver, Elif Kose
Tarkuc, Simge
BARAN, Derya
Tanyeli, Cihangir
Toppare, Levent Kamil

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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 pi-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 lambda(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.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/36295

Journal

TETRAHEDRON LETTERS

DOI

https://doi.org/10.1016/j.tetlet.2011.03.078

Collections

Department of Chemistry, Article

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Citation Formats

E. K. Unver, S. Tarkuc, D. BARAN, C. Tanyeli, and L. K. Toppare, “Synthesis of new donor-acceptor polymers containing thiadiazoloquinoxaline and pyrazinoquinoxaline moieties: low-band gap, high optical contrast, and almost black colored materials,” TETRAHEDRON LETTERS, pp. 2725–2729, 2011, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/36295.