Thermal stability, solubility, and fluorescence property of poly(arylene vinylene ketone)s bearing 1,1′-binaphthylene units

Tadashi Tsukamoto; Katsuya Maeyama; Shuhei Higashibayashi; Hidehiro Sakurai

doi:10.1016/j.reactfunctpolym.2016.01.014

Thermal stability, solubility, and fluorescence property of poly(arylene vinylene ketone)s bearing 1,1′-binaphthylene units

Tadashi Tsukamoto, Katsuya Maeyama, Shuhei Higashibayashi, Hidehiro Sakurai

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

Mizoroki-Heck coupling polymerization of diiodonated 1,1′-binaphthyls (BINTL1/BINTL2) with 1,4-divinylbenzenes (DVB-H/DVB-Me/DVB-OMe) proceeded to afford poly(arylene vinylene ketone)s (PAVK1-6). Upon photoexcitation, PAVKs in solutions exhibit fluorescence behavior with large Stokes shifts, and the maximum emission wavelength (λ_em) depends on the nature of the solvent. PAVK1 analogs, in which the ketone carbonyl units of PAVK1 are replaced by sulfone, methylene, and ketal ones, were synthesized. Fluorescence spectra of PAVK1 analogs clearly exhibit a blue shift from that of original PAVK1. The difference in behavior between PAVKs and PAVK1 analogs suggests that the fluorescence of PAVKs originates from donor-acceptor interaction between 1,4-distryrylbenzene skeletons and ketone carbonyl units, respectively.

Original language	English
Pages (from-to)	123-129
Number of pages	7
Journal	Reactive and Functional Polymers
Volume	100
DOIs	https://doi.org/10.1016/j.reactfunctpolym.2016.01.014
Publication status	Published - 2016 Mar 1
Externally published	Yes

Keywords

Fluorescence property
Mizoroki-Heck coupling polymerization
Poly(arylene vinylene ketone)
Solvatochromism
Thermal stability

ASJC Scopus subject areas

Materials Chemistry
Polymers and Plastics
Chemistry(all)
Chemical Engineering(all)
Environmental Chemistry
Biochemistry

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@article{9bd20ae61a2b42379bf78709e3f4d521,

title = "Thermal stability, solubility, and fluorescence property of poly(arylene vinylene ketone)s bearing 1,1′-binaphthylene units",

abstract = "Mizoroki-Heck coupling polymerization of diiodonated 1,1′-binaphthyls (BINTL1/BINTL2) with 1,4-divinylbenzenes (DVB-H/DVB-Me/DVB-OMe) proceeded to afford poly(arylene vinylene ketone)s (PAVK1-6). Upon photoexcitation, PAVKs in solutions exhibit fluorescence behavior with large Stokes shifts, and the maximum emission wavelength (λem) depends on the nature of the solvent. PAVK1 analogs, in which the ketone carbonyl units of PAVK1 are replaced by sulfone, methylene, and ketal ones, were synthesized. Fluorescence spectra of PAVK1 analogs clearly exhibit a blue shift from that of original PAVK1. The difference in behavior between PAVKs and PAVK1 analogs suggests that the fluorescence of PAVKs originates from donor-acceptor interaction between 1,4-distryrylbenzene skeletons and ketone carbonyl units, respectively.",

keywords = "Fluorescence property, Mizoroki-Heck coupling polymerization, Poly(arylene vinylene ketone), Solvatochromism, Thermal stability",

author = "Tadashi Tsukamoto and Katsuya Maeyama and Shuhei Higashibayashi and Hidehiro Sakurai",

year = "2016",

month = mar,

day = "1",

doi = "10.1016/j.reactfunctpolym.2016.01.014",

language = "English",

volume = "100",

pages = "123--129",

journal = "Reactive and Functional Polymers",

issn = "1381-5148",

publisher = "Elsevier",

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T1 - Thermal stability, solubility, and fluorescence property of poly(arylene vinylene ketone)s bearing 1,1′-binaphthylene units

AU - Tsukamoto, Tadashi

AU - Maeyama, Katsuya

AU - Higashibayashi, Shuhei

AU - Sakurai, Hidehiro

PY - 2016/3/1

Y1 - 2016/3/1

N2 - Mizoroki-Heck coupling polymerization of diiodonated 1,1′-binaphthyls (BINTL1/BINTL2) with 1,4-divinylbenzenes (DVB-H/DVB-Me/DVB-OMe) proceeded to afford poly(arylene vinylene ketone)s (PAVK1-6). Upon photoexcitation, PAVKs in solutions exhibit fluorescence behavior with large Stokes shifts, and the maximum emission wavelength (λem) depends on the nature of the solvent. PAVK1 analogs, in which the ketone carbonyl units of PAVK1 are replaced by sulfone, methylene, and ketal ones, were synthesized. Fluorescence spectra of PAVK1 analogs clearly exhibit a blue shift from that of original PAVK1. The difference in behavior between PAVKs and PAVK1 analogs suggests that the fluorescence of PAVKs originates from donor-acceptor interaction between 1,4-distryrylbenzene skeletons and ketone carbonyl units, respectively.

AB - Mizoroki-Heck coupling polymerization of diiodonated 1,1′-binaphthyls (BINTL1/BINTL2) with 1,4-divinylbenzenes (DVB-H/DVB-Me/DVB-OMe) proceeded to afford poly(arylene vinylene ketone)s (PAVK1-6). Upon photoexcitation, PAVKs in solutions exhibit fluorescence behavior with large Stokes shifts, and the maximum emission wavelength (λem) depends on the nature of the solvent. PAVK1 analogs, in which the ketone carbonyl units of PAVK1 are replaced by sulfone, methylene, and ketal ones, were synthesized. Fluorescence spectra of PAVK1 analogs clearly exhibit a blue shift from that of original PAVK1. The difference in behavior between PAVKs and PAVK1 analogs suggests that the fluorescence of PAVKs originates from donor-acceptor interaction between 1,4-distryrylbenzene skeletons and ketone carbonyl units, respectively.

KW - Fluorescence property

KW - Mizoroki-Heck coupling polymerization

KW - Poly(arylene vinylene ketone)

KW - Solvatochromism

KW - Thermal stability

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