Synthesis and fluorescence emission properties of D-π-D monomers based on dithieno[3,2-b:2′,3′-d]thiophene

Wang, Chuan-Zeng; Do, Jung-Hee; Akther, Tahmina; Feng, Xing; Matsumoto, Taisuke; Tanaka, Junji; Redshaw, Carl; Yamato, Takehiko

Abstract

We herein present four highly fluorescent and stable D-π-D monomers (2), which were designed and synthesized using different types of aryl substituent as the donor via a Suzuki-Miyaura coupling reaction. We have studied these four symmetrical chromophores by UV–vis absorption and fluorescence emission spectroscopy both in solution and the solid state. This research shows that the introduction of the aryl groups can effectively reduced the HOMO-LUMO gap of thiophene chromophore resulting in a shift of the wavelength of the absorption and fluorescence emission. The notable optical features of their solid-state powders also exhibited a distinct red-shift in comparison with the emissions of their dilute solutions. These results combined with the theoretical calculations (B3LYP/6–31G*) indicate that these systems are promising candidates in the fabrication of organic electroluminescence devices.

Citation

Wang, C.-Z., Do, J.-H., Akther, T., Feng, X., Matsumoto, T., Tanaka, J., Redshaw, C., & Yamato, T. (2017). Synthesis and fluorescence emission properties of D-π-D monomers based on dithieno[3,2-b:2′,3′-d]thiophene. Journal of Luminescence, 188(388), 388-393. https://doi.org/10.1016/j.jlumin.2017.04.060

• Journal Article Type: Article
• Acceptance Date: Apr 27, 2017
• Online Publication Date: Apr 28, 2017
• Publication Date: 2017-08
• Deposit Date: Aug 18, 2017
• Publicly Available Date: May 1, 2018
• Journal: Journal of luminescence
• Print ISSN: 0022-2313
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 188
• Issue: 388
• Pages: 388-393
• DOI: https://doi.org/10.1016/j.jlumin.2017.04.060
• Keywords: Biophysics; Atomic and Molecular Physics, and Optics; Biochemistry; General Chemistry; Condensed Matter Physics
• Public URL: https://hull-repository.worktribe.com/output/454192
• Publisher URL: http://www.sciencedirect.com/science/article/pii/S0022231317300662
• Additional Information: This is the accepted manuscript of an article published in Journal of luminescence, 2017. The version of record is available at the DOI link in this record.
• Contract Date: May 1, 2018