Design and synthesis of laser-activatable tetrazoles for a fast and fluorogenic red-emitting 1,3-dipolar cycloaddition reaction

Peng An; Zhipeng Yu; Qing Lin

doi:10.1021/ol402645q

Design and synthesis of laser-activatable tetrazoles for a fast and fluorogenic red-emitting 1,3-dipolar cycloaddition reaction

Peng An
, Zhipeng Yu
, Qing Lin

Chemistry

SUNY Buffalo

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

48 Scopus citations

Abstract

The design and synthesis of a new class of laser light activatable tetrazoles with extended π-systems is reported. Upon 405 nm laser light irradiation, these bithiophene-substituted tetrazoles underwent extremely fast 1,3-dipolar cycloaddition reactions with dimethyl fumarate with second-order rate constants approaching 4000 M^-1 s^-1. The resulting pyrazoline cycloadducts exhibited solvent-dependent red fluorescence, making these tetrazoles potentially useful as fluorogenic probes for detecting alkenes in vivo.

Original language	English
Pages (from-to)	5496-5499
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	21
DOIs	https://doi.org/10.1021/ol402645q
State	Published - Nov 1 2013

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title = "Design and synthesis of laser-activatable tetrazoles for a fast and fluorogenic red-emitting 1,3-dipolar cycloaddition reaction",

abstract = "The design and synthesis of a new class of laser light activatable tetrazoles with extended π-systems is reported. Upon 405 nm laser light irradiation, these bithiophene-substituted tetrazoles underwent extremely fast 1,3-dipolar cycloaddition reactions with dimethyl fumarate with second-order rate constants approaching 4000 M-1 s-1. The resulting pyrazoline cycloadducts exhibited solvent-dependent red fluorescence, making these tetrazoles potentially useful as fluorogenic probes for detecting alkenes in vivo.",

author = "Peng An and Zhipeng Yu and Qing Lin",

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doi = "10.1021/ol402645q",

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journal = "Organic Letters",

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AU - An, Peng

AU - Yu, Zhipeng

AU - Lin, Qing

PY - 2013/11/1

Y1 - 2013/11/1

N2 - The design and synthesis of a new class of laser light activatable tetrazoles with extended π-systems is reported. Upon 405 nm laser light irradiation, these bithiophene-substituted tetrazoles underwent extremely fast 1,3-dipolar cycloaddition reactions with dimethyl fumarate with second-order rate constants approaching 4000 M-1 s-1. The resulting pyrazoline cycloadducts exhibited solvent-dependent red fluorescence, making these tetrazoles potentially useful as fluorogenic probes for detecting alkenes in vivo.

AB - The design and synthesis of a new class of laser light activatable tetrazoles with extended π-systems is reported. Upon 405 nm laser light irradiation, these bithiophene-substituted tetrazoles underwent extremely fast 1,3-dipolar cycloaddition reactions with dimethyl fumarate with second-order rate constants approaching 4000 M-1 s-1. The resulting pyrazoline cycloadducts exhibited solvent-dependent red fluorescence, making these tetrazoles potentially useful as fluorogenic probes for detecting alkenes in vivo.

UR - https://www.scopus.com/pages/publications/84887061479

U2 - 10.1021/ol402645q

DO - 10.1021/ol402645q

M3 - Article

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AN - SCOPUS:84887061479

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EP - 5499

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Design and synthesis of laser-activatable tetrazoles for a fast and fluorogenic red-emitting 1,3-dipolar cycloaddition reaction

Abstract

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