Reversible Disassembly-Assembly of Octa Acid-Guest Capsule in Water Triggered by a Photochromic Process

A. Mohan Raj; Françisco M. Raymo; V. Ramamurthy

doi:10.1021/acs.orglett.6b00405

Reversible Disassembly-Assembly of Octa Acid-Guest Capsule in Water Triggered by a Photochromic Process

A. Mohan Raj, Françisco M. Raymo, V. Ramamurthy

Chemistry

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

19 Scopus citations

Abstract

Octa acid (OA), a calixarene-based cavitand, forms a 1:2 capsular assembly with neutral 1,3,3-trimethyl-6′-nitrospiro[2H-1]benzopyran-2,2′-indoline and 1:1 cavitandplex with its open zwitterionic merocyanine form. Photochromic interconversion between the spiropyran and merocyanine leads to unprecedented reversible capsular disassembly and assembly. OA provides stability to the merocyanine in both the ground and excited states. The photochemically controlled disassembly and assembly process established here points toward the opportunity of using the OA capsule in delivering small molecules at the desired locations.

Original language	English (US)
Pages (from-to)	1566-1569
Number of pages	4
Journal	Organic letters
Volume	18
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.6b00405
State	Published - Apr 15 2016

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Reversible Disassembly-Assembly of Octa Acid-Guest Capsule in Water Triggered by a Photochromic Process",

abstract = "Octa acid (OA), a calixarene-based cavitand, forms a 1:2 capsular assembly with neutral 1,3,3-trimethyl-6′-nitrospiro[2H-1]benzopyran-2,2′-indoline and 1:1 cavitandplex with its open zwitterionic merocyanine form. Photochromic interconversion between the spiropyran and merocyanine leads to unprecedented reversible capsular disassembly and assembly. OA provides stability to the merocyanine in both the ground and excited states. The photochemically controlled disassembly and assembly process established here points toward the opportunity of using the OA capsule in delivering small molecules at the desired locations.",

author = "{Mohan Raj}, A. and Raymo, {Fran{\c c}isco M.} and V. Ramamurthy",

note = "Funding Information: V.R. thanks the National Science Foundation (CHE-1411458) for financial support. Publisher Copyright: {\textcopyright} 2016 American Chemical Society. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.",

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doi = "10.1021/acs.orglett.6b00405",

language = "English (US)",

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AU - Mohan Raj, A.

AU - Raymo, Françisco M.

AU - Ramamurthy, V.

N1 - Funding Information: V.R. thanks the National Science Foundation (CHE-1411458) for financial support. Publisher Copyright: © 2016 American Chemical Society. Copyright: Copyright 2016 Elsevier B.V., All rights reserved.

PY - 2016/4/15

Y1 - 2016/4/15

N2 - Octa acid (OA), a calixarene-based cavitand, forms a 1:2 capsular assembly with neutral 1,3,3-trimethyl-6′-nitrospiro[2H-1]benzopyran-2,2′-indoline and 1:1 cavitandplex with its open zwitterionic merocyanine form. Photochromic interconversion between the spiropyran and merocyanine leads to unprecedented reversible capsular disassembly and assembly. OA provides stability to the merocyanine in both the ground and excited states. The photochemically controlled disassembly and assembly process established here points toward the opportunity of using the OA capsule in delivering small molecules at the desired locations.

AB - Octa acid (OA), a calixarene-based cavitand, forms a 1:2 capsular assembly with neutral 1,3,3-trimethyl-6′-nitrospiro[2H-1]benzopyran-2,2′-indoline and 1:1 cavitandplex with its open zwitterionic merocyanine form. Photochromic interconversion between the spiropyran and merocyanine leads to unprecedented reversible capsular disassembly and assembly. OA provides stability to the merocyanine in both the ground and excited states. The photochemically controlled disassembly and assembly process established here points toward the opportunity of using the OA capsule in delivering small molecules at the desired locations.

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Reversible Disassembly-Assembly of Octa Acid-Guest Capsule in Water Triggered by a Photochromic Process

Abstract

ASJC Scopus subject areas

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