A Photobasic Functional Group

Jie He; Flora W. Kimani; John C. Jewett

doi:10.1021/jacs.5b04367

A Photobasic Functional Group

Jie He, Flora W. Kimani, John C. Jewett

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

27 Scopus citations

Abstract

Controlling chemical reactivity using light is a longstanding practice within organic chemistry, yet little has been done to modulate the basicity of compounds. Reported herein is a triazabutadiene that is rendered basic upon photoisomerization. The pH of an aqueous solution containing the water-soluble triazabutadiene can be adjusted with 350 nm light. Upon synthesizing a triazabutadiene that is soluble in aprotic organic solvents, we noted a similar light-induced change in basicity. As a proof of concept we took this photobase and used it to catalyze a condensation reaction.

Original language	English (US)
Pages (from-to)	9764-9767
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	31
DOIs	https://doi.org/10.1021/jacs.5b04367
State	Published - Aug 12 2015

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.5b04367

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abstract = "Controlling chemical reactivity using light is a longstanding practice within organic chemistry, yet little has been done to modulate the basicity of compounds. Reported herein is a triazabutadiene that is rendered basic upon photoisomerization. The pH of an aqueous solution containing the water-soluble triazabutadiene can be adjusted with 350 nm light. Upon synthesizing a triazabutadiene that is soluble in aprotic organic solvents, we noted a similar light-induced change in basicity. As a proof of concept we took this photobase and used it to catalyze a condensation reaction.",

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AU - He, Jie

AU - Kimani, Flora W.

AU - Jewett, John C.

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AB - Controlling chemical reactivity using light is a longstanding practice within organic chemistry, yet little has been done to modulate the basicity of compounds. Reported herein is a triazabutadiene that is rendered basic upon photoisomerization. The pH of an aqueous solution containing the water-soluble triazabutadiene can be adjusted with 350 nm light. Upon synthesizing a triazabutadiene that is soluble in aprotic organic solvents, we noted a similar light-induced change in basicity. As a proof of concept we took this photobase and used it to catalyze a condensation reaction.

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A Photobasic Functional Group

Abstract

ASJC Scopus subject areas

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