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A Defect‐Free Naphthalene Diimide Bithiazole Copolymer via Regioselective Direct Arylation Polycondensation
Author(s) -
Matsidik Rukiya,
Giorgio Michele,
Luzio Alessandro,
Caironi Mario,
Komber Hartmut,
Sommer Michael
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800821
Subject(s) - chemistry , regioselectivity , homo/lumo , monomer , condensation polymer , nucleophilic substitution , structural isomer , diimide , copolymer , thermal stability , combinatorial chemistry , polymer chemistry , stereochemistry , molecule , organic chemistry , polymer , catalysis , perylene
An optimized direct arylation polycondensation (DAP) protocol for the synthesis of a novel naphthalene diimide (NDI) 2,2′‐bithiazole (2‐BTz) copolymer (PNDI‐2‐BTz) is presented. The regioselective C–H activation of 2‐BTz at the 5‐positions allows for the synthesis of fully regioregular and homocoupling‐free PNDI‐2‐BTz of high molecular weight in less than 1 h in quantitative yield. Complete end group assignment shows functionalities according to monomer structures or to nucleophilic substitution, and allows for the reliable determination of absolute molecular weight. Compared to the well‐known bithiophene analog PNDIT2, an exceptionally high thermal stability, a hypsochromically shifted charge transfer absorption band and a lower‐lying LUMO energy level is found, making PNDI‐2‐BTz an interesting candidate for applications in organic electronic devices. In contrast to the selective and high yielding C–H activation of 2‐BTz at the 5‐position, the regioisomer 5,5′‐bithiazole is inactive under a variety of conditions.