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The Impact of C(2) Insertion into a Carbazole Donor on the Physicochemical Properties of Dibenzo[a,j]phenazine‐Cored Donor–Acceptor–Donor Triads

Novel electron donor–acceptor–donor (D‐A‐D) compounds comprising dibenzo[a,j]phenazine as the central acceptor core and two 7‐membered diarylamines (iminodibenzyl and iminostilbene) as the donors have been designed and synthesized. Investigation of their physicochemical properties revealed the impac...

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Autores principales: Zimmermann Crocomo, Paola, Kaihara, Takahito, Kawaguchi., Soki, Stachelek, Patrycja, Minakata, Satoshi, de Silva, Piotr, Data, Przemyslaw, Takeda, Youhei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8519004/
https://www.ncbi.nlm.nih.gov/pubmed/34314537
http://dx.doi.org/10.1002/chem.202101654
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author Zimmermann Crocomo, Paola
Kaihara, Takahito
Kawaguchi., Soki
Stachelek, Patrycja
Minakata, Satoshi
de Silva, Piotr
Data, Przemyslaw
Takeda, Youhei
author_facet Zimmermann Crocomo, Paola
Kaihara, Takahito
Kawaguchi., Soki
Stachelek, Patrycja
Minakata, Satoshi
de Silva, Piotr
Data, Przemyslaw
Takeda, Youhei
author_sort Zimmermann Crocomo, Paola
collection PubMed
description Novel electron donor–acceptor–donor (D‐A‐D) compounds comprising dibenzo[a,j]phenazine as the central acceptor core and two 7‐membered diarylamines (iminodibenzyl and iminostilbene) as the donors have been designed and synthesized. Investigation of their physicochemical properties revealed the impact of C(2) insertion into well‐known carbazole electron donors on the properties of previously reported twisted dibenzo[a,j]phenazine‐core D‐A‐D triads. Slight structural modification caused a drastic change in conformational preference, allowing unique photophysical behavior of dual emission derived from room‐temperature phosphorescence and triplet–triplet annihilation. Furthermore, electrochemical analysis suggested sigma‐dimer formation and electrochemical polymerization on the electrode. Quantum chemical calculations also rationalized the experimental results.
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spelling pubmed-85190042021-10-21 The Impact of C(2) Insertion into a Carbazole Donor on the Physicochemical Properties of Dibenzo[a,j]phenazine‐Cored Donor–Acceptor–Donor Triads Zimmermann Crocomo, Paola Kaihara, Takahito Kawaguchi., Soki Stachelek, Patrycja Minakata, Satoshi de Silva, Piotr Data, Przemyslaw Takeda, Youhei Chemistry Full Papers Novel electron donor–acceptor–donor (D‐A‐D) compounds comprising dibenzo[a,j]phenazine as the central acceptor core and two 7‐membered diarylamines (iminodibenzyl and iminostilbene) as the donors have been designed and synthesized. Investigation of their physicochemical properties revealed the impact of C(2) insertion into well‐known carbazole electron donors on the properties of previously reported twisted dibenzo[a,j]phenazine‐core D‐A‐D triads. Slight structural modification caused a drastic change in conformational preference, allowing unique photophysical behavior of dual emission derived from room‐temperature phosphorescence and triplet–triplet annihilation. Furthermore, electrochemical analysis suggested sigma‐dimer formation and electrochemical polymerization on the electrode. Quantum chemical calculations also rationalized the experimental results. John Wiley and Sons Inc. 2021-08-13 2021-09-20 /pmc/articles/PMC8519004/ /pubmed/34314537 http://dx.doi.org/10.1002/chem.202101654 Text en © 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Zimmermann Crocomo, Paola
Kaihara, Takahito
Kawaguchi., Soki
Stachelek, Patrycja
Minakata, Satoshi
de Silva, Piotr
Data, Przemyslaw
Takeda, Youhei
The Impact of C(2) Insertion into a Carbazole Donor on the Physicochemical Properties of Dibenzo[a,j]phenazine‐Cored Donor–Acceptor–Donor Triads
title The Impact of C(2) Insertion into a Carbazole Donor on the Physicochemical Properties of Dibenzo[a,j]phenazine‐Cored Donor–Acceptor–Donor Triads
title_full The Impact of C(2) Insertion into a Carbazole Donor on the Physicochemical Properties of Dibenzo[a,j]phenazine‐Cored Donor–Acceptor–Donor Triads
title_fullStr The Impact of C(2) Insertion into a Carbazole Donor on the Physicochemical Properties of Dibenzo[a,j]phenazine‐Cored Donor–Acceptor–Donor Triads
title_full_unstemmed The Impact of C(2) Insertion into a Carbazole Donor on the Physicochemical Properties of Dibenzo[a,j]phenazine‐Cored Donor–Acceptor–Donor Triads
title_short The Impact of C(2) Insertion into a Carbazole Donor on the Physicochemical Properties of Dibenzo[a,j]phenazine‐Cored Donor–Acceptor–Donor Triads
title_sort impact of c(2) insertion into a carbazole donor on the physicochemical properties of dibenzo[a,j]phenazine‐cored donor–acceptor–donor triads
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8519004/
https://www.ncbi.nlm.nih.gov/pubmed/34314537
http://dx.doi.org/10.1002/chem.202101654
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