Structural-Functional Properties of Asymmetric Fluoro-Alkoxy Substituted Benzothiadiazole Homopolymers with Flanked Chalcogen-Based Heterocycles. Academic Article uri icon


  • The synthesis and characterization of asymmetric alkoxy- are reported, fluoro-benzothiadiazole (BT) acceptor core derivatized with a series of six different heterocycles (selenophene, thiophene, furan, 5-thiazole, 2-thiazole and 2-oxazole). The effect of the flanked-heterocycles containing different chalcogen atoms of the six homopolymers (HPX) is studied using optical, thermal, electrochemical, and computational analysis. Computational calculations indicate a strong relationship between the most stable conformation for each homopolymer and their bearing heterocycle, thus homopolymers HPSe', HPTp', HPFu', and HPTzC5, adopted the syn-syn and syn-anti conformations due to their noncovalent interactions with shorter distances, while HPTzC2' and HPOx' demonstrate preference for the anti-anti conformation. Optical property studies of the homopolymers reveal a strong red-shift in solution and film upon exchanging the chalcogen atom from Oxygen < Sulfur < Selenium in HPFu, HPTp, and HPSe, respectively. In addition, deeper highest occupied molecular orbital (HOMO) energy levels are observed when the donor-acceptor moieties (HPSe, HPTp, and HPFu) are substituted for the acceptor-acceptor systems such as HPTzC5, HPTzC2, and HPOx. Improved packing and morphology are exhibited for the donor-acceptor homopolymers. Thus, having a flanked heterocycle containing different chalcogen-atoms in polymeric systems is one way of tuning the physicochemical properties of conjugated materials for optoelectronic applications.

published proceedings

  • Macromol Rapid Commun

altmetric score

  • 2.6

author list (cited authors)

  • Com, M., Moncho, S., Attar, S., Barg, M., Brothers, E., Bazzi, H. S., & Al-Hashimi, M.

citation count

  • 1

complete list of authors

  • Comí, Marc||Moncho, Salvador||Attar, Salahuddin||Barłóg, Maciej||Brothers, Edward||Bazzi, Hassan S||Al-Hashimi, Mohammed

publication date

  • February 2023