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

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

Chemistry

Research output: Contribution to journal › Article

6 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

Fingerprint

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Cite this

Kamatham, N., Da Silva, J. P., Givens, R. S., & Ramamurthy, V. (2017). Melding Caged Compounds with Supramolecular Containers: Photogeneration and Miscreant Behavior of the Coumarylmethyl Carbocation. Organic Letters, 19(13), 3588-3591. https://doi.org/10.1021/acs.orglett.7b01572

@article{f55a0715890a4f16b2e8d0c38d9ddf72,

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 Vaidhyanathan Ramamurthy",

year = "2017",

month = jul

day = "7",

doi = "10.1021/acs.orglett.7b01572",

language = "English (US)",

volume = "19",

pages = "3588--3591",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "13",

}

TY - JOUR

T1 - Melding Caged Compounds with Supramolecular Containers

T2 - Photogeneration and Miscreant Behavior of the Coumarylmethyl Carbocation

AU - Kamatham, Nareshbabu

AU - Da Silva, José P.

AU - Givens, Richard S.

AU - Ramamurthy, Vaidhyanathan

PY - 2017/7/7

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.

UR - http://www.scopus.com/inward/record.url?scp=85022339843&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85022339843&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.7b01572

DO - 10.1021/acs.orglett.7b01572

M3 - Article

AN - SCOPUS:85022339843

VL - 19

SP - 3588

EP - 3591

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 13

ER -

Access to Document

10.1021/acs.orglett.7b01572