Push–Pull-Type Polychlorotriphenylmethyl Radicals: New Two-Photon Absorbers and Dyes for Generation of Photo-Charges

Xiaojin Wu; Jun Oh Kim; Samara Medina; Francisco J. Ramírez; Paula Mayorga Burrezo; Shaofei Wu; Zheng Long Lim; Christoph Lambert; Juan Casado; Dongho Kim; Jishan Wu

doi:10.1002/chem.201701875

Push–Pull-Type Polychlorotriphenylmethyl Radicals: New Two-Photon Absorbers and Dyes for Generation of Photo-Charges

Xiaojin Wu, Jun Oh Kim, Samara Medina, Francisco J. Ramírez, Paula Mayorga Burrezo, Shaofei Wu, Zheng Long Lim, Christoph Lambert, Juan Casado, Dongho Kim, Jishan Wu

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

21 Citations (Scopus)

Abstract

Tri(4-iodo-2,3,5,6-tetrachlorophenyl)methane (2) is reported as a general building block for the synthesis of various π-conjugated polychlorotriphenylmethyl (PTM) radicals. Three push–pull-type triphenylamine-substituted PTM radicals with different substitution patterns were prepared and all exhibited intense inter-valence charge-transfer bands and large two-photon absorption (TPA) cross sections. Moreover, increase of solvent polarity also resulted in improved TPA response. The charge-transfer character of the relevant excited states provoked the efficient photo-generation of charges, anions in the PTM and cations in the amine arms, driven by the amphoteric redox character and the small coupling between donor and acceptor.

Original language	English
Pages (from-to)	7698-7702
Number of pages	5
Journal	Chemistry - A European Journal
Volume	23
Issue number	32
DOIs	https://doi.org/10.1002/chem.201701875
Publication status	Published - 2017 Jun 7

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Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

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10.1002/chem.201701875

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title = "Push–Pull-Type Polychlorotriphenylmethyl Radicals: New Two-Photon Absorbers and Dyes for Generation of Photo-Charges",

abstract = "Tri(4-iodo-2,3,5,6-tetrachlorophenyl)methane (2) is reported as a general building block for the synthesis of various π-conjugated polychlorotriphenylmethyl (PTM) radicals. Three push–pull-type triphenylamine-substituted PTM radicals with different substitution patterns were prepared and all exhibited intense inter-valence charge-transfer bands and large two-photon absorption (TPA) cross sections. Moreover, increase of solvent polarity also resulted in improved TPA response. The charge-transfer character of the relevant excited states provoked the efficient photo-generation of charges, anions in the PTM and cations in the amine arms, driven by the amphoteric redox character and the small coupling between donor and acceptor.",

author = "Xiaojin Wu and Kim, {Jun Oh} and Samara Medina and Ram{\'i}rez, {Francisco J.} and {Mayorga Burrezo}, Paula and Shaofei Wu and Lim, {Zheng Long} and Christoph Lambert and Juan Casado and Dongho Kim and Jishan Wu",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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language = "English",

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T1 - Push–Pull-Type Polychlorotriphenylmethyl Radicals

T2 - New Two-Photon Absorbers and Dyes for Generation of Photo-Charges

AU - Wu, Xiaojin

AU - Kim, Jun Oh

AU - Medina, Samara

AU - Ramírez, Francisco J.

AU - Mayorga Burrezo, Paula

AU - Wu, Shaofei

AU - Lim, Zheng Long

AU - Lambert, Christoph

AU - Casado, Juan

AU - Kim, Dongho

AU - Wu, Jishan

PY - 2017/6/7

Y1 - 2017/6/7

N2 - Tri(4-iodo-2,3,5,6-tetrachlorophenyl)methane (2) is reported as a general building block for the synthesis of various π-conjugated polychlorotriphenylmethyl (PTM) radicals. Three push–pull-type triphenylamine-substituted PTM radicals with different substitution patterns were prepared and all exhibited intense inter-valence charge-transfer bands and large two-photon absorption (TPA) cross sections. Moreover, increase of solvent polarity also resulted in improved TPA response. The charge-transfer character of the relevant excited states provoked the efficient photo-generation of charges, anions in the PTM and cations in the amine arms, driven by the amphoteric redox character and the small coupling between donor and acceptor.

AB - Tri(4-iodo-2,3,5,6-tetrachlorophenyl)methane (2) is reported as a general building block for the synthesis of various π-conjugated polychlorotriphenylmethyl (PTM) radicals. Three push–pull-type triphenylamine-substituted PTM radicals with different substitution patterns were prepared and all exhibited intense inter-valence charge-transfer bands and large two-photon absorption (TPA) cross sections. Moreover, increase of solvent polarity also resulted in improved TPA response. The charge-transfer character of the relevant excited states provoked the efficient photo-generation of charges, anions in the PTM and cations in the amine arms, driven by the amphoteric redox character and the small coupling between donor and acceptor.

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ER -

Push–Pull-Type Polychlorotriphenylmethyl Radicals: New Two-Photon Absorbers and Dyes for Generation of Photo-Charges

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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