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Synthesis of Poly(arylene vinylene)s with Different End Groups by Combining Acyclic Diene Metathesis Polymerization with Wittig‐type Couplings
Author(s) -
Miyashita Tomonari,
Kunisawa Mikiko,
Sueki Shunsuke,
Nomura Kotohiro
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201700466
Subject(s) - wittig reaction , metathesis , polymerization , polymer chemistry , acyclic diene metathesis , arylene , chemistry , atom transfer radical polymerization , end group , copolymer , organic chemistry , polymer , aryl , alkyl
A series of end‐functionalized poly(9,9′‐di‐ n ‐octylfluorene vinylene)s (EF‐PFVs) with different end groups were obtained by 1) synthesizing EF‐PFV with vinyl end groups by acyclic diene metathesis (ADMET) polymerization with a molybdenum catalyst and termination with an aldehyde and 2) subsequent olefin metathesis of the vinyl group with the molybdenum catalyst followed by Wittig‐type coupling with another aldehyde. The exclusive formation of EF‐PFVs containing a vinyl end group by the ADMET polymerization was confirmed by grafting PEG, and by the synthesis of amphiphilic triblock copolymers by combining atom transfer radical polymerization from the PFV chain end with PEG grafting through a click reaction. Various EF‐PFVs with different end groups, such as C 6 F 5 , pyridyl, ferrocenyl, and terthiophene, have thus been prepared. Their fluorescence spectra (e.g., intensities, emission wavelengths) were influenced by the end groups and the length of the conjugation.