Synthesis and characterizations of star-shaped octupolar triazatruxenes-based two-photon absorption chromophores

Jinjun Shao; Zhenping Guan; Yongli Yan; Chongjun Jiao; Qing Hua Xu; Chunyan Chi

doi:10.1021/jo1017926

Synthesis and characterizations of star-shaped octupolar triazatruxenes-based two-photon absorption chromophores

Jinjun Shao, Zhenping Guan, Yongli Yan, Chongjun Jiao, Qing Hua Xu, Chunyan Chi

National University of Singapore

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

116 Scopus citations

Abstract

A series of star-shaped octupolar triazatruxenes (TATs, 1-6) with intramolecular "push-pull" structure were synthesized and their photophysical properties have been systematically investigated. These chromophores showed obvious solvatochromic effect, i.e., significant bathochromic shift of the emission spectra and larger Stokes shifts were observed in more polar solvents mainly due to photoinduced intramolecular charge transfer (ICT). The two-photon absorption (2PA) cross-section values were determined by two-photon excited fluorescence (2PEF) measurements in toluene and THF. These chromophores exhibited large two-photon absorption cross-sections ranging from 280 to 1620GM in the near-infrared (NIR) region. Compound 6 showed the largest 2PA action crosssection (σF) of 564 GM and could be a potential two-photon fluorescent (2PF) probe. In addition, compounds 1-6 all displayed good thermal stability and photostability.

Original language	English
Pages (from-to)	780-790
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	76
Issue number	3
DOIs	https://doi.org/10.1021/jo1017926
State	Published - 4 Feb 2011
Externally published	Yes

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title = "Synthesis and characterizations of star-shaped octupolar triazatruxenes-based two-photon absorption chromophores",

abstract = "A series of star-shaped octupolar triazatruxenes (TATs, 1-6) with intramolecular {"}push-pull{"} structure were synthesized and their photophysical properties have been systematically investigated. These chromophores showed obvious solvatochromic effect, i.e., significant bathochromic shift of the emission spectra and larger Stokes shifts were observed in more polar solvents mainly due to photoinduced intramolecular charge transfer (ICT). The two-photon absorption (2PA) cross-section values were determined by two-photon excited fluorescence (2PEF) measurements in toluene and THF. These chromophores exhibited large two-photon absorption cross-sections ranging from 280 to 1620GM in the near-infrared (NIR) region. Compound 6 showed the largest 2PA action crosssection (σF) of 564 GM and could be a potential two-photon fluorescent (2PF) probe. In addition, compounds 1-6 all displayed good thermal stability and photostability.",

author = "Jinjun Shao and Zhenping Guan and Yongli Yan and Chongjun Jiao and Xu, {Qing Hua} and Chunyan Chi",

year = "2011",

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T1 - Synthesis and characterizations of star-shaped octupolar triazatruxenes-based two-photon absorption chromophores

AU - Shao, Jinjun

AU - Guan, Zhenping

AU - Yan, Yongli

AU - Jiao, Chongjun

AU - Xu, Qing Hua

AU - Chi, Chunyan

PY - 2011/2/4

Y1 - 2011/2/4

N2 - A series of star-shaped octupolar triazatruxenes (TATs, 1-6) with intramolecular "push-pull" structure were synthesized and their photophysical properties have been systematically investigated. These chromophores showed obvious solvatochromic effect, i.e., significant bathochromic shift of the emission spectra and larger Stokes shifts were observed in more polar solvents mainly due to photoinduced intramolecular charge transfer (ICT). The two-photon absorption (2PA) cross-section values were determined by two-photon excited fluorescence (2PEF) measurements in toluene and THF. These chromophores exhibited large two-photon absorption cross-sections ranging from 280 to 1620GM in the near-infrared (NIR) region. Compound 6 showed the largest 2PA action crosssection (σF) of 564 GM and could be a potential two-photon fluorescent (2PF) probe. In addition, compounds 1-6 all displayed good thermal stability and photostability.

AB - A series of star-shaped octupolar triazatruxenes (TATs, 1-6) with intramolecular "push-pull" structure were synthesized and their photophysical properties have been systematically investigated. These chromophores showed obvious solvatochromic effect, i.e., significant bathochromic shift of the emission spectra and larger Stokes shifts were observed in more polar solvents mainly due to photoinduced intramolecular charge transfer (ICT). The two-photon absorption (2PA) cross-section values were determined by two-photon excited fluorescence (2PEF) measurements in toluene and THF. These chromophores exhibited large two-photon absorption cross-sections ranging from 280 to 1620GM in the near-infrared (NIR) region. Compound 6 showed the largest 2PA action crosssection (σF) of 564 GM and could be a potential two-photon fluorescent (2PF) probe. In addition, compounds 1-6 all displayed good thermal stability and photostability.

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DO - 10.1021/jo1017926

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SN - 0022-3263

VL - 76

SP - 780

EP - 790

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 3

ER -

Synthesis and characterizations of star-shaped octupolar triazatruxenes-based two-photon absorption chromophores

Abstract

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