Melding Caged Compounds with Supramolecular Containers: Photogeneration and Miscreant Behavior of the Coumarylmethyl Carbocation

Nareshbabu Kamatham; José P. Da Silva; Richard S. Givens; V. Ramamurthy

doi:10.1021/acs.orglett.7b01572

Melding Caged Compounds with Supramolecular Containers: Photogeneration and Miscreant Behavior of the Coumarylmethyl Carbocation

Nareshbabu Kamatham, José P. Da Silva, Richard S. Givens, V. Ramamurthy

Chemistry

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

9 Scopus citations

Abstract

By merging well-established concepts of supramolecular chemistry, protecting group strategy, and photochemistry, we have solubilized in water hydrophobic organic molecules consisting of a photoactive protecting group and masked carboxylic acids, released the desired acid, and confined a reactive carbocation intermediate within a capsule. Confinement of the photogenerated carbocation brought out the latent radical-like behavior. This observation is consistent with the recent theoretical prediction of the 7-(diethylamino)coumarinyl-4-methyl carbocation having a triplet diradical ground-state electronic contribution.

Original language	English (US)
Pages (from-to)	3588-3591
Number of pages	4
Journal	Organic letters
Volume	19
Issue number	13
DOIs	https://doi.org/10.1021/acs.orglett.7b01572
State	Published - Jul 7 2017

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.7b01572

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title = "Melding Caged Compounds with Supramolecular Containers: Photogeneration and Miscreant Behavior of the Coumarylmethyl Carbocation",

abstract = "By merging well-established concepts of supramolecular chemistry, protecting group strategy, and photochemistry, we have solubilized in water hydrophobic organic molecules consisting of a photoactive protecting group and masked carboxylic acids, released the desired acid, and confined a reactive carbocation intermediate within a capsule. Confinement of the photogenerated carbocation brought out the latent radical-like behavior. This observation is consistent with the recent theoretical prediction of the 7-(diethylamino)coumarinyl-4-methyl carbocation having a triplet diradical ground-state electronic contribution.",

author = "Nareshbabu Kamatham and {Da Silva}, {Jos{\'e} P.} and Givens, {Richard S.} and V. Ramamurthy",

note = "Funding Information: The National Science Foundation (CHE-1411458), FCT-Foundation for Science and Technology (UID/Multi/04326/2013), and Kansas University Endowment Association, respectively, are thanked by V.R., JPDS and RSG for financial support. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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AU - Da Silva, José P.

AU - Givens, Richard S.

AU - Ramamurthy, V.

N1 - Funding Information: The National Science Foundation (CHE-1411458), FCT-Foundation for Science and Technology (UID/Multi/04326/2013), and Kansas University Endowment Association, respectively, are thanked by V.R., JPDS and RSG for financial support. Publisher Copyright: © 2017 American Chemical Society.

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Y1 - 2017/7/7

N2 - By merging well-established concepts of supramolecular chemistry, protecting group strategy, and photochemistry, we have solubilized in water hydrophobic organic molecules consisting of a photoactive protecting group and masked carboxylic acids, released the desired acid, and confined a reactive carbocation intermediate within a capsule. Confinement of the photogenerated carbocation brought out the latent radical-like behavior. This observation is consistent with the recent theoretical prediction of the 7-(diethylamino)coumarinyl-4-methyl carbocation having a triplet diradical ground-state electronic contribution.

AB - By merging well-established concepts of supramolecular chemistry, protecting group strategy, and photochemistry, we have solubilized in water hydrophobic organic molecules consisting of a photoactive protecting group and masked carboxylic acids, released the desired acid, and confined a reactive carbocation intermediate within a capsule. Confinement of the photogenerated carbocation brought out the latent radical-like behavior. This observation is consistent with the recent theoretical prediction of the 7-(diethylamino)coumarinyl-4-methyl carbocation having a triplet diradical ground-state electronic contribution.

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Melding Caged Compounds with Supramolecular Containers: Photogeneration and Miscreant Behavior of the Coumarylmethyl Carbocation

Abstract

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