Premium
Selective Synthesis and Properties of Electron‐Deficient Hybrid Naphthalene‐Based π‐Conjugated Systems
Author(s) -
Mikie Tsubasa,
Osaka Itaru
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201803208
Subject(s) - conjugated system , naphthalene , ring (chemistry) , polymer , materials science , quinoxaline , reagent , photochemistry , combinatorial chemistry , chemistry , organic chemistry
One driving force for advancing the field of semiconducting polymers is to create new π‐conjugated systems as building units. This work reports on a series of electron‐deficient hybrid naphthalene‐based π‐conjugated systems in which two different units among benzoxadiazole, benzothiadiazole, benzoselenadiazole, and benzopyrazine (quinoxaline) were fused. These π‐conjugated systems were synthesized in excellent yields via the selective one‐side ring‐opening reaction of corresponding naphthobischalcogenadiazoles using the NaBH 4 /CoCl 2 reduction reagents, followed by the ring‐closing reactions. The electronic structure of these π‐conjugated systems was studied in comparison with their parent systems. Furthermore, thiadiazolonaphthoxadiazole was incorporated into the π‐conjugated polymer backbone. The electronic structure, film structure, and photovoltaic properties of the polymer were studied as well.