Control of Photoisomerization of an Azoazacryptand by Anion Binding and Cucurbit[8]uril Encapsulation in an Aqueous Solution

Oshchepkov AS, Namashivaya SSR, Khrustalev VN, Hampel F, Laikov DN, Kataev E (2020)

Publication Type: Journal article

Publication year: 2020

Journal

Journal of Organic Chemistry American Chemical Society

Book Volume: 85

Pages Range: 9255-9263

Journal Issue: 14

DOI: 10.1021/acs.joc.0c01260

Abstract

Control of isomerization of a receptor bearing multiple light-switchable subunits in a confined space is critical for the design of synthetic molecular machines. Toward this goal, a new azacryptand containing three azobenzene subunits has been developed, and its photoisomerization in an aqueous solution has been studied depending on anion coordination and recognition by a larger host-cucurbit[8]uril (CB[8]). The cryptand in its hexaprotonated form shows considerable affinity for fluoride and perchlorate, which in turn affects the isomer distribution of the receptor under UV-light irradiation, stabilizing the isomers of the cryptand with Z-configurations. CB[8] was found to be able to encapsulate the isomers of the cryptand by forming a Matryoshka-type complex. The irradiation of a 10:1 CB[8]-cryptand mixture has led to a selective conversion of the cryptand to the E,E,Z isomer inside CB[8]. It has been demonstrated that the addition of fluoride to the resulted complex induces the release of the cryptand as a major E,E,E isomer, while other studied anions were ineffective in this reaction. To our knowledge, this work presents a first example of a host-controlled photoisomerization of an anion receptor bearing multiple switching azobenzenes that model the function of naturally occurring chaperones.

Authors with CRIS profile

Frank Hampel Lehrstuhl für Organische Chemie I Evgeny Kataev Lehrstuhl für Organische Chemie I

Involved external institutions

Technische Universität Chemnitz DE Germany (DE) Peoples' Friendship University of Russia RU Russian Federation (RU) Lomonosov Moscow State University / Московский государственный университет имени М.В.Ломоносова RU Russian Federation (RU)

How to cite

APA:

Oshchepkov, A.S., Namashivaya, S.S.R., Khrustalev, V.N., Hampel, F., Laikov, D.N., & Kataev, E. (2020). Control of Photoisomerization of an Azoazacryptand by Anion Binding and Cucurbit[8]uril Encapsulation in an Aqueous Solution. Journal of Organic Chemistry, 85(14), 9255-9263. https://doi.org/10.1021/acs.joc.0c01260

MLA:

Oshchepkov, Aleksandr S., et al. "Control of Photoisomerization of an Azoazacryptand by Anion Binding and Cucurbit[8]uril Encapsulation in an Aqueous Solution." Journal of Organic Chemistry 85.14 (2020): 9255-9263.

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