Parviainen, T. A. O., Salmela, P. M., Sippola, R. J., & Heiskanen, J. P. (2022). Syntheses of thiophene and thiazole-based building blocks and their utilization in the syntheses of a-d-a type organic semiconducting materials with dithienosilolo central unit. ACS Omega, 7(30), 26328–26335. https://doi.org/10.1021/acsomega.2c02195
Syntheses of thiophene and thiazole-based building blocks and their utilization in the syntheses of A-D-A type organic semiconducting materials with dithienosilolo central unit
|Author:||Parviainen, Tomi A. O.1; Salmela, Petri M.1; Sippola, Roosa J.1;|
1Research Unit of Sustainable Chemistry, University of Oulu, P.O. Box 4300, FI-90014 Oulu, Finland
|Online Access:||PDF Full Text (PDF, 1.6 MB)|
|Persistent link:|| http://urn.fi/urn:nbn:fi-fe2022082556333
American Chemical Society,
|Publish Date:|| 2022-08-25
Dithienosilole moiety is an electron donating unit, and it has been applied, for example, as a part of small molecular and polymeric electron donors in high performance organic photovoltaic cells. Herein, we report efficient synthetic routes to two symmetrical, dithienosilolo-central-unit-based A-D-A type organic semiconducting materials DTS(Th₂FBTTh)₂ and DTS(ThFBTTh)₂. Fine-tuned conditions in Suzuki–Miyaura couplings were tested and utilized. The effect of inserting additional hexylthiophene structures symmetrically into the material backbone was investigated, and it was noted that contrary to commonly accepted fact, the distance between electron donor and acceptor seems to play a bigger role in lowering the Egap value of the molecule than just extending the length of the conjugated backbone. We searched for precedent cases from the literature, and these are compared to our findings. The optical properties of the materials were characterized with UV–vis spectroscopy. Majority of the intermediate compounds along the way to final products were produced with excellent yields. Our results offer highly efficient routes to many heterocyclic structures but also give new insights into the design of organic semiconducting materials.
|Pages:||26328 - 26335|
|Type of Publication:||
A1 Journal article – refereed
|Field of Science:||
116 Chemical sciences
© 2022 The Authors. Published by American Chemical Society.