Triphenylamine/4,4′-Dimethoxytriphenylamine-Functionalized Thieno[3,2-b]thiophene Fluorophores with a High Quantum Efficiency: Synthesis and Photophysical Properties

Isci R., Unal M., Kucukcakir G., Gurbuz N. A., Gorkem S. F., Öztürk T.

Journal of Physical Chemistry B, vol.125, no.48, pp.13309-13319, 2021 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 125 Issue: 48
  • Publication Date: 2021
  • Doi Number: 10.1021/acs.jpcb.1c09448
  • Journal Name: Journal of Physical Chemistry B
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Applied Science & Technology Source, Aquatic Science & Fisheries Abstracts (ASFA), Chemical Abstracts Core, Chimica, Compendex, Computer & Applied Sciences, EMBASE, MEDLINE
  • Page Numbers: pp.13309-13319
  • Istanbul Technical University Affiliated: Yes

Abstract

A wide series of 10 new triphenylamine (TPA)/4,4′-dimethoxytriphenylamine (TPA(OMe)2)-functionalized thieno[3,2-b]thiophene (TT) fluorophores,4a-eand5a-e, bearing different electron-donating and electron-withdrawing substituents (-PhCN, -PhF, -PhOMe, -Ph, and -C6H13) at the terminal thienothiophene units were designed and synthesized by the Suzuki coupling reaction. Their optical and electrochemical properties were investigated by experimental and computational studies. Solid-state fluorescent quantum yields were recorded to be from 20 to 69%, and the maximum solution-state quantum efficiency reached 97%. Moreover, the photophysical characterization of the novel chromophores demonstrated a significant Stokes shift, reaching 179 nm with a bathochromic shift. They exhibited tuning color emission from orange to dark blue in solution and showed fluorescence lifetime reaching 4.70 ns. The relationship between triphenylamine (TPA)/4,4′-dimethoxytriphenylamine (TPA(OMe)2)-derived triarylamines and different functional groups on thieno[3,2-b] thiophene units was discussed.