Synthesis of Poly(arylene vinylene)s with Different End Groups by Combining Acyclic Diene Metathesis Polymerization with Wittig-type Couplings
Tomonari Miyashita
Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, 1-1 Minami Osawa, Hachioji, Tokyo, 192-0376 Japan
These authors contributed equally to this work.
Search for more papers by this authorMikiko Kunisawa
Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, 1-1 Minami Osawa, Hachioji, Tokyo, 192-0376 Japan
These authors contributed equally to this work.
Search for more papers by this authorDr. Shunsuke Sueki
Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, 1-1 Minami Osawa, Hachioji, Tokyo, 192-0376 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Kotohiro Nomura
Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, 1-1 Minami Osawa, Hachioji, Tokyo, 192-0376 Japan
Search for more papers by this authorTomonari Miyashita
Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, 1-1 Minami Osawa, Hachioji, Tokyo, 192-0376 Japan
These authors contributed equally to this work.
Search for more papers by this authorMikiko Kunisawa
Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, 1-1 Minami Osawa, Hachioji, Tokyo, 192-0376 Japan
These authors contributed equally to this work.
Search for more papers by this authorDr. Shunsuke Sueki
Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, 1-1 Minami Osawa, Hachioji, Tokyo, 192-0376 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Kotohiro Nomura
Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, 1-1 Minami Osawa, Hachioji, Tokyo, 192-0376 Japan
Search for more papers by this authorGraphical Abstract
Which is the end? Conjugated polymers based on poly(9,9′-di-n-octylfluorene vinylene) with different end groups were synthesized by combining molybdenum-catalyzed acyclic diene metathesis polymerization with a subsequent Wittig-type coupling. Their fluorescence spectra were influenced by the end groups and the conjugation length.
Abstract
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 C6F5, 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.
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