The Impact of C2 Insertion into a Carbazole Donor on the Physicochemical Properties of Dibenzo[a,j]phenazine-Cored Donor-Acceptor-Donor Triads

Paola Zimmermann Crocomo; Takahito Kaihara; Soki Kawaguchi; Patrycja Stachelek; Satoshi Minakata; Piotr de Silva; Przemyslaw Data; Youhei Takeda

doi:10.1002/chem.202101654

The Impact of C₂ Insertion into a Carbazole Donor on the Physicochemical Properties of Dibenzo[a,j]phenazine-Cored Donor-Acceptor-Donor Triads

Paola Zimmermann Crocomo, Takahito Kaihara, Soki Kawaguchi, Patrycja Stachelek, Satoshi Minakata, Piotr de Silva^*, Przemyslaw Data^*, Youhei Takeda^*

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › Research › peer-review

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Abstract

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 C₂ 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.

Original language	English
Journal	Chemistry - A European Journal
Volume	27
Issue number	53
Pages (from-to)	13390-13398
Number of pages	9
ISSN	0947-6539
DOIs	https://doi.org/10.1002/chem.202101654
Publication status	Published - 2021

Keywords

Charge transfer
Donor-acceptor
Fluorescence
Organic light-emitting diodes
Triplet-triplet annihilation

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title = "The Impact of C2 Insertion into a Carbazole Donor on the Physicochemical Properties of Dibenzo[a,j]phenazine-Cored Donor-Acceptor-Donor Triads",

abstract = "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 C2 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.",

keywords = "Charge transfer, Donor-acceptor, Fluorescence, Organic light-emitting diodes, Triplet-triplet annihilation",

author = "{Zimmermann Crocomo}, Paola and Takahito Kaihara and Soki Kawaguchi and Patrycja Stachelek and Satoshi Minakata and {de Silva}, Piotr and Przemyslaw Data and Youhei Takeda",

year = "2021",

doi = "10.1002/chem.202101654",

language = "English",

volume = "27",

pages = "13390--13398",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley",

number = "53",

}

The Impact of C₂ 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 et al.
In: Chemistry - A European Journal, Vol. 27, No. 53, 2021, p. 13390-13398.

Research output: Contribution to journal › Journal article › Research › peer-review

TY - JOUR

T1 - The Impact of C2 Insertion into a Carbazole Donor on the Physicochemical Properties of Dibenzo[a,j]phenazine-Cored Donor-Acceptor-Donor Triads

AU - Zimmermann Crocomo, Paola

AU - Kaihara, Takahito

AU - Kawaguchi, Soki

AU - Stachelek, Patrycja

AU - Minakata, Satoshi

AU - de Silva, Piotr

AU - Data, Przemyslaw

AU - Takeda, Youhei

PY - 2021

Y1 - 2021

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AB - 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 C2 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.

KW - Charge transfer

KW - Donor-acceptor

KW - Fluorescence

KW - Organic light-emitting diodes

KW - Triplet-triplet annihilation

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DO - 10.1002/chem.202101654

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SN - 0947-6539

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JO - Chemistry - A European Journal

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