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 | |
| State | Published - Jul 7 2017 |
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ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
Melding Caged Compounds with Supramolecular Containers : Photogeneration and Miscreant Behavior of the Coumarylmethyl Carbocation. / Kamatham, Nareshbabu; Da Silva, José P.; Givens, Richard S.; Ramamurthy, Vaidhyanathan.
In: Organic Letters, Vol. 19, No. 13, 07.07.2017, p. 3588-3591.Research output: Contribution to journal › Article
}
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 -