Synthesis, photophysics, and electrochemistry of thiophene–pyridine and thiophene–pyrimidine dyad comonomers

Author:

Bolduc Andréanne1,Dufresne Stéphane1,Hanan Garry S.1,Skene W. G.1

Affiliation:

1. Centre for Self-Assembled Chemical Structures, Département de Chimie, Université de Montréal, CP 6128, Succ. Centre-ville, Montréal, QC H3C 3J7, Canada.

Abstract

A series of new π-conjugated donor (D) and acceptor (A) dyad comonomers were prepared using Suzuki coupling protocols. The D–A comonomers consisting of thiophene/bithiophene as donors and pyridine/pyrimidine as acceptors were prepared to investigate their photophysical and electrochemical properties. The dyads were spectroscopically confirmed to be highly conjugated. This was further supported by the X-ray crystal structure of the bithophene–pyridine dyad that showed all the heterocycles to be coplanar. It was further found that the fluorescence yields (Φfl) of the dyads were highly dependent on the number of thiophenes. The bithiophene derivatives exhibited Φfl values ≥ 0.3 while the thiophene derivatives did not fluoresce. The suppressed fluorescence observed for the thiophene derivatives was due to their higher triplet energy resulting in efficient intersystem crossing (ISC) to the triplet state with ΦISC ≥ 0.8. This was confirmed both by time-resolved and steady-state measurements. The singlet excited state of both thiophene and bithiophene dyads was deactivated solely by either fluorescence and (or) ISC. Owing to their donor and acceptor character, the dyads could be oxidized and reduced both electrochemically and photochemically to afford the radical cation and anion, respectively.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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