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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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Detalles Bibliográficos
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
Descripción
Sumario: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.