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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...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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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. |
format | Online Article Text |
id | pubmed-8519004 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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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