Improved functionality and control in the isomerization of a calix[4]arene-capped azobenzene

Paul A. Bonvallet; Max R. Mullen; Paul J. Evans; Kristen L. Stoltz; Erica N. Story

doi:10.1016/j.tetlet.2010.12.107

Improved functionality and control in the isomerization of a calix[4]arene-capped azobenzene

Paul A. Bonvallet, Max R. Mullen, Paul J. Evans, Kristen L. Stoltz, Erica N. Story

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

15 Scopus citations

Abstract

An improved azobenzene core capped by two calix[4]arene units isomerizes readily between trans and cis configurations via photochemical and/or thermal means. In addition, the presence of acid (particularly HCl) increases the rate of thermal cis→trans conversion. These enhancements to the functional response, control, and understanding of calixarene-capped azobenzene isomerization are important for future application in the dynamic encapsulation of small chemical species.

Original language	English (US)
Pages (from-to)	1117-1120
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	10
DOIs	https://doi.org/10.1016/j.tetlet.2010.12.107
State	Published - Mar 9 2011
Externally published	Yes

Bibliographical note

Funding Information:
This work was funded by the College of Wooster , the Copeland Fund for Independent Study , the Wilson Fund , and NSF Grants CHE-9977546 and CHE-0704026 . We thank the Mass Spectrometry Center of the University of Akron and the Department of Macromolecular Science and Engineering at Case Western Reserve University ( NSF Grant CHE-0821515 ) for instrumental support.

Keywords

Azobenzene
Calixarene
Photoisomerization
Stimuli-responsive material
Thermal isomerization

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abstract = "An improved azobenzene core capped by two calix[4]arene units isomerizes readily between trans and cis configurations via photochemical and/or thermal means. In addition, the presence of acid (particularly HCl) increases the rate of thermal cis→trans conversion. These enhancements to the functional response, control, and understanding of calixarene-capped azobenzene isomerization are important for future application in the dynamic encapsulation of small chemical species.",

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AU - Bonvallet, Paul A.

AU - Mullen, Max R.

AU - Evans, Paul J.

AU - Stoltz, Kristen L.

AU - Story, Erica N.

N1 - Funding Information: This work was funded by the College of Wooster , the Copeland Fund for Independent Study , the Wilson Fund , and NSF Grants CHE-9977546 and CHE-0704026 . We thank the Mass Spectrometry Center of the University of Akron and the Department of Macromolecular Science and Engineering at Case Western Reserve University ( NSF Grant CHE-0821515 ) for instrumental support.

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AB - An improved azobenzene core capped by two calix[4]arene units isomerizes readily between trans and cis configurations via photochemical and/or thermal means. In addition, the presence of acid (particularly HCl) increases the rate of thermal cis→trans conversion. These enhancements to the functional response, control, and understanding of calixarene-capped azobenzene isomerization are important for future application in the dynamic encapsulation of small chemical species.

KW - Azobenzene

KW - Calixarene

KW - Photoisomerization

KW - Stimuli-responsive material

KW - Thermal isomerization

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Improved functionality and control in the isomerization of a calix[4]arene-capped azobenzene

Abstract

Bibliographical note

Keywords

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