D-π-D chromophores based on dithieno[3,2-b:2′,3'-d]thiophene (DTT) : potential application in the fabrication of solar cell

Akther, Tahmina; Feng, Xing; Elsegood, Mark R.J.; Elsegood, Mark Ri; Wang, Chuan-Zeng; Do, Jung-Hee; Akther, Thamina; Xing, Feng; Horsburgh, Lynne; Elsegood, Mark; Redshaw, Carl; Yamato, Takehiko

Abstract

In this work, four stable dithieno[3,2-b:2′,3'-d]thiophene-based π-extended molecules were designed and synthesized via a Pd-catalysed Sonogashira coupling reaction. The structures of these symmetrical compounds, including dithieno[3,2-b:2′,3'-d]thiophene (DTT) as the π-center and various donor (D) groups, were determined on the basis of NMR spectral data, elemental analysis, and X-ray crystallography. The photo-physical properties of the DTT-based derivatives 2 were fully investigated in both solution and solid state. The notable optical features of their solid-state powders showed significant red-shift in comparison with the luminescence of their dilute dichloromethane solutions. These results combined with the theoretical calculations indicate that they are promising candidates for the several applications in electronic and optoelectronic devices, as well as organic dyes for solar cells.

Citation

Akther, T., Feng, X., Elsegood, M. R., Elsegood, M. R., Wang, C., Do, J., …Yamato, T. (2017). D-π-D chromophores based on dithieno[3,2-b:2′,3'-d]thiophene (DTT) : potential application in the fabrication of solar cell. Tetrahedron, 73(4), 307-312. https://doi.org/10.1016/j.tet.2016.11.077

• Acceptance Date: Nov 30, 2016
• Online Publication Date: Dec 3, 2016
• Publication Date: Jan 1, 2017
• Deposit Date: Dec 14, 2016
• Publicly Available Date: Dec 12, 2017
• Journal: Tetrahedron
• Print ISSN: 0040-4020
• Electronic ISSN: 1464-5416
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 73
• Issue: 4
• Pages: 307-312
• DOI: https://doi.org/10.1016/j.tet.2016.11.077
• Keywords: Organic Chemistry; Biochemistry; Drug Discovery
• Public URL: https://hull-repository.worktribe.com/output/472185
• Publisher URL: http://www.sciencedirect.com/science/article/pii/S0040402016312571
• Additional Information: This article is maintained by: Elsevier; Article Title: D-π-D chromophores based on dithieno[3,2-b:2',3'-d]thiophene (DTT): Potential application in the fabrication of solar cell; Journal Title: Tetrahedron; CrossRef DOI link to publisher maintained version: http://dx.doi.org/10.1016/j.tet.2016.11.077; Content Type: article; Copyright: © 2016 Elsevier Ltd. All rights reserved.