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Synthesis and Characterization of White-Light Luminescent End-Capped Polyimides Based on FRET and Excited State Intramolecular Proton Transfer

N-cyclohexylphthalimide-substituted trifluoroacetylamino (CF(3)CONH-) group (3TfAPI), which forms an intramolecular hydrogen bond, was synthesized, and it exhibited a bright yellow fluorescence owing to the excited-state intramolecular proton transfer (ESIPT) in the solution and crystalline states....

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Autores principales: Tabuchi, Atsuko, Hayakawa, Teruaki, Kuwata, Shigeki, Ishige, Ryohei, Ando, Shinji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8621099/
https://www.ncbi.nlm.nih.gov/pubmed/34833349
http://dx.doi.org/10.3390/polym13224050
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author Tabuchi, Atsuko
Hayakawa, Teruaki
Kuwata, Shigeki
Ishige, Ryohei
Ando, Shinji
author_facet Tabuchi, Atsuko
Hayakawa, Teruaki
Kuwata, Shigeki
Ishige, Ryohei
Ando, Shinji
author_sort Tabuchi, Atsuko
collection PubMed
description N-cyclohexylphthalimide-substituted trifluoroacetylamino (CF(3)CONH-) group (3TfAPI), which forms an intramolecular hydrogen bond, was synthesized, and it exhibited a bright yellow fluorescence owing to the excited-state intramolecular proton transfer (ESIPT) in the solution and crystalline states. In addition, CF(3)CONH-substituted phthalic anhydride (3TfAPA) was synthesized, which was attached to the termini of a blue-fluorescent semi-aromatic polyimide (PI) chain. Owing to the efficient Förster resonance energy transfer (FRET) occurring from the main chain to the termini and the suppression of deprotonation (anion formation) at the 3TfAPA moiety by H(2)SO(4) doping, the resulting PI films display bright white fluorescence. Moreover, the enhancement of the chain rigidity by substituting the diamine moiety results in an increase in the quantum yield of white fluorescence (Φ) by a factor of 1.7, due to the suppression of local molecular motion. This material design strategy is promising for preparing thermally stable white-light fluorescent PIs applicable to solar spectral convertors, displays, and ICT devices.
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spelling pubmed-86210992021-11-27 Synthesis and Characterization of White-Light Luminescent End-Capped Polyimides Based on FRET and Excited State Intramolecular Proton Transfer Tabuchi, Atsuko Hayakawa, Teruaki Kuwata, Shigeki Ishige, Ryohei Ando, Shinji Polymers (Basel) Article N-cyclohexylphthalimide-substituted trifluoroacetylamino (CF(3)CONH-) group (3TfAPI), which forms an intramolecular hydrogen bond, was synthesized, and it exhibited a bright yellow fluorescence owing to the excited-state intramolecular proton transfer (ESIPT) in the solution and crystalline states. In addition, CF(3)CONH-substituted phthalic anhydride (3TfAPA) was synthesized, which was attached to the termini of a blue-fluorescent semi-aromatic polyimide (PI) chain. Owing to the efficient Förster resonance energy transfer (FRET) occurring from the main chain to the termini and the suppression of deprotonation (anion formation) at the 3TfAPA moiety by H(2)SO(4) doping, the resulting PI films display bright white fluorescence. Moreover, the enhancement of the chain rigidity by substituting the diamine moiety results in an increase in the quantum yield of white fluorescence (Φ) by a factor of 1.7, due to the suppression of local molecular motion. This material design strategy is promising for preparing thermally stable white-light fluorescent PIs applicable to solar spectral convertors, displays, and ICT devices. MDPI 2021-11-22 /pmc/articles/PMC8621099/ /pubmed/34833349 http://dx.doi.org/10.3390/polym13224050 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Tabuchi, Atsuko
Hayakawa, Teruaki
Kuwata, Shigeki
Ishige, Ryohei
Ando, Shinji
Synthesis and Characterization of White-Light Luminescent End-Capped Polyimides Based on FRET and Excited State Intramolecular Proton Transfer
title Synthesis and Characterization of White-Light Luminescent End-Capped Polyimides Based on FRET and Excited State Intramolecular Proton Transfer
title_full Synthesis and Characterization of White-Light Luminescent End-Capped Polyimides Based on FRET and Excited State Intramolecular Proton Transfer
title_fullStr Synthesis and Characterization of White-Light Luminescent End-Capped Polyimides Based on FRET and Excited State Intramolecular Proton Transfer
title_full_unstemmed Synthesis and Characterization of White-Light Luminescent End-Capped Polyimides Based on FRET and Excited State Intramolecular Proton Transfer
title_short Synthesis and Characterization of White-Light Luminescent End-Capped Polyimides Based on FRET and Excited State Intramolecular Proton Transfer
title_sort synthesis and characterization of white-light luminescent end-capped polyimides based on fret and excited state intramolecular proton transfer
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8621099/
https://www.ncbi.nlm.nih.gov/pubmed/34833349
http://dx.doi.org/10.3390/polym13224050
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