Porphyrin–Azobenzene–Bodipy Triads: Syntheses, Structures, and Photophysical Properties

Bangshao Yin, Taeyeon Kim, Mingbo Zhou, Weiming Huang, Dongho Kim, Jianxin Song

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Cyclic and acyclic azobenzene bridged porphyrin−dipyrrin derivatives were successfully prepared via Suzuki−Miyaura coupling reaction of α,α′-diborylated dipyrromethane with bromoazophenyl porphyrin or reaction of borylated porphyrin with dibromoazophenyl dipyrrin, and the corresponding porphyrin−Bodipy derivatives were obtained by subsequent boron complexation. The cyclic porphyrin−dipyrrin compound 3Ni was confirmed by X-ray diffraction. The low fluorescence quantum yields of azobenzene bridged porphyrin−Bodipy can be ascribed to the presence of the intramolecular charge transfer state.
Original languageEnglish
Pages (from-to)2654-2657
Number of pages4
JournalOrganic Letters
Volume19
Issue number10
DOIs
Publication statusPublished - 2017 May 19

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Porphyrins
porphyrins
cyclic compounds
Derivatives
Boron
Quantum yield
synthesis
Complexation
X-Ray Diffraction
Charge transfer
boron
Fluorescence
charge transfer
X ray diffraction
fluorescence
diffraction
x rays
azobenzene
dipyrromethane

Cite this

Yin, Bangshao ; Kim, Taeyeon ; Zhou, Mingbo ; Huang, Weiming ; Kim, Dongho ; Song, Jianxin. / Porphyrin–Azobenzene–Bodipy Triads: Syntheses, Structures, and Photophysical Properties. In: Organic Letters. 2017 ; Vol. 19, No. 10. pp. 2654-2657.
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abstract = "Cyclic and acyclic azobenzene bridged porphyrin−dipyrrin derivatives were successfully prepared via Suzuki−Miyaura coupling reaction of α,α′-diborylated dipyrromethane with bromoazophenyl porphyrin or reaction of borylated porphyrin with dibromoazophenyl dipyrrin, and the corresponding porphyrin−Bodipy derivatives were obtained by subsequent boron complexation. The cyclic porphyrin−dipyrrin compound 3Ni was confirmed by X-ray diffraction. The low fluorescence quantum yields of azobenzene bridged porphyrin−Bodipy can be ascribed to the presence of the intramolecular charge transfer state.",
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Porphyrin–Azobenzene–Bodipy Triads: Syntheses, Structures, and Photophysical Properties. / Yin, Bangshao; Kim, Taeyeon; Zhou, Mingbo; Huang, Weiming; Kim, Dongho; Song, Jianxin.

In: Organic Letters, Vol. 19, No. 10, 19.05.2017, p. 2654-2657.

Research output: Contribution to journalArticle

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T1 - Porphyrin–Azobenzene–Bodipy Triads: Syntheses, Structures, and Photophysical Properties

AU - Yin, Bangshao

AU - Kim, Taeyeon

AU - Zhou, Mingbo

AU - Huang, Weiming

AU - Kim, Dongho

AU - Song, Jianxin

PY - 2017/5/19

Y1 - 2017/5/19

N2 - Cyclic and acyclic azobenzene bridged porphyrin−dipyrrin derivatives were successfully prepared via Suzuki−Miyaura coupling reaction of α,α′-diborylated dipyrromethane with bromoazophenyl porphyrin or reaction of borylated porphyrin with dibromoazophenyl dipyrrin, and the corresponding porphyrin−Bodipy derivatives were obtained by subsequent boron complexation. The cyclic porphyrin−dipyrrin compound 3Ni was confirmed by X-ray diffraction. The low fluorescence quantum yields of azobenzene bridged porphyrin−Bodipy can be ascribed to the presence of the intramolecular charge transfer state.

AB - Cyclic and acyclic azobenzene bridged porphyrin−dipyrrin derivatives were successfully prepared via Suzuki−Miyaura coupling reaction of α,α′-diborylated dipyrromethane with bromoazophenyl porphyrin or reaction of borylated porphyrin with dibromoazophenyl dipyrrin, and the corresponding porphyrin−Bodipy derivatives were obtained by subsequent boron complexation. The cyclic porphyrin−dipyrrin compound 3Ni was confirmed by X-ray diffraction. The low fluorescence quantum yields of azobenzene bridged porphyrin−Bodipy can be ascribed to the presence of the intramolecular charge transfer state.

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