A Family of Highly Fluorescent and Unsymmetric Bis(BF
                        2
                        ) Chromophore Containing Both Pyrrole and N-Heteroarene Derivatives: BOPPY

Changjiang Yu; Zhenlong Huang; Xinru Wang; Wei Miao; Qinghua Wu; Wai Yeung Wong; Erhong Hao; Yi Xiao; Lijuan Jiao

doi:10.1021/acs.orglett.8b01752

A Family of Highly Fluorescent and Unsymmetric Bis(BF ₂ ) Chromophore Containing Both Pyrrole and N-Heteroarene Derivatives: BOPPY

Changjiang Yu, Zhenlong Huang, Xinru Wang, Wei Miao, Qinghua Wu, Wai Yeung Wong, Erhong Hao, Yi Xiao, Lijuan Jiao

Research output: Journal article publication › Journal article › Academic research › peer-review

63 Citations (Scopus)

Abstract

A fundamental, highly fluorescent, and easily accessible scaffold named BOPPY is reported. The use of hydrazine as a bridging linkage between pyrrole and N-heteroarenes enables the binding of two BF ₂ units to provide sufficient rigidity of the unsymmetric core skeleton. These resultant unsymmetrical BOPPYs are thus highly fluorescent in their solutions and solid powder states and exhibit high molar absorption coefficients (42200-47000 M ^-1 cm ^-1 ), large Stokes shifts, excellent photostability, and insensitivity to pH. More importantly, these BOPPYs showed efficient two-photon absorption in the wide spectral range of 700-900 nm, making them well suited for two-photon fluorescence microscopy imaging in living cells.

Original language	English
Pages (from-to)	4462-4466
Number of pages	5
Journal	Organic Letters
Volume	20
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.8b01752
Publication status	Published - 3 Aug 2018

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b01752

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title = "A Family of Highly Fluorescent and Unsymmetric Bis(BF 2 ) Chromophore Containing Both Pyrrole and N-Heteroarene Derivatives: BOPPY",

abstract = " A fundamental, highly fluorescent, and easily accessible scaffold named BOPPY is reported. The use of hydrazine as a bridging linkage between pyrrole and N-heteroarenes enables the binding of two BF 2 units to provide sufficient rigidity of the unsymmetric core skeleton. These resultant unsymmetrical BOPPYs are thus highly fluorescent in their solutions and solid powder states and exhibit high molar absorption coefficients (42200-47000 M -1 cm -1 ), large Stokes shifts, excellent photostability, and insensitivity to pH. More importantly, these BOPPYs showed efficient two-photon absorption in the wide spectral range of 700-900 nm, making them well suited for two-photon fluorescence microscopy imaging in living cells. ",

author = "Changjiang Yu and Zhenlong Huang and Xinru Wang and Wei Miao and Qinghua Wu and Wong, {Wai Yeung} and Erhong Hao and Yi Xiao and Lijuan Jiao",

year = "2018",

month = aug,

day = "3",

doi = "10.1021/acs.orglett.8b01752",

language = "English",

volume = "20",

pages = "4462--4466",

journal = "Organic Letters",

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publisher = "American Chemical Society",

number = "15",

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A Family of Highly Fluorescent and Unsymmetric Bis(BF ₂ ) Chromophore Containing Both Pyrrole and N-Heteroarene Derivatives: BOPPY. / Yu, Changjiang; Huang, Zhenlong; Wang, Xinru et al.
In: Organic Letters, Vol. 20, No. 15, 03.08.2018, p. 4462-4466.

Research output: Journal article publication › Journal article › Academic research › peer-review

TY - JOUR

T1 - A Family of Highly Fluorescent and Unsymmetric Bis(BF 2 ) Chromophore Containing Both Pyrrole and N-Heteroarene Derivatives

T2 - BOPPY

AU - Yu, Changjiang

AU - Huang, Zhenlong

AU - Wang, Xinru

AU - Miao, Wei

AU - Wu, Qinghua

AU - Wong, Wai Yeung

AU - Hao, Erhong

AU - Xiao, Yi

AU - Jiao, Lijuan

PY - 2018/8/3

Y1 - 2018/8/3

N2 - A fundamental, highly fluorescent, and easily accessible scaffold named BOPPY is reported. The use of hydrazine as a bridging linkage between pyrrole and N-heteroarenes enables the binding of two BF 2 units to provide sufficient rigidity of the unsymmetric core skeleton. These resultant unsymmetrical BOPPYs are thus highly fluorescent in their solutions and solid powder states and exhibit high molar absorption coefficients (42200-47000 M -1 cm -1 ), large Stokes shifts, excellent photostability, and insensitivity to pH. More importantly, these BOPPYs showed efficient two-photon absorption in the wide spectral range of 700-900 nm, making them well suited for two-photon fluorescence microscopy imaging in living cells.

AB - A fundamental, highly fluorescent, and easily accessible scaffold named BOPPY is reported. The use of hydrazine as a bridging linkage between pyrrole and N-heteroarenes enables the binding of two BF 2 units to provide sufficient rigidity of the unsymmetric core skeleton. These resultant unsymmetrical BOPPYs are thus highly fluorescent in their solutions and solid powder states and exhibit high molar absorption coefficients (42200-47000 M -1 cm -1 ), large Stokes shifts, excellent photostability, and insensitivity to pH. More importantly, these BOPPYs showed efficient two-photon absorption in the wide spectral range of 700-900 nm, making them well suited for two-photon fluorescence microscopy imaging in living cells.

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U2 - 10.1021/acs.orglett.8b01752

DO - 10.1021/acs.orglett.8b01752

M3 - Journal article

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SN - 1523-7060

VL - 20

SP - 4462

EP - 4466

JO - Organic Letters

JF - Organic Letters

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ER -

A Family of Highly Fluorescent and Unsymmetric Bis(BF ₂ ) Chromophore Containing Both Pyrrole and N-Heteroarene Derivatives: BOPPY

Abstract

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