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Supramolecular Chemistry Volume 26, 2014 - Issue 3-4: Eighth International Symposium of Macrocyclic and Supramolecular Chemistry (ISMSC-8)
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Articles

Synthesis of a Zn-salen resorcinarene-based cavitand and its fluorescence response to nitro compounds

Yujin LeeDepartment of Chemistry and Biochemistry, Brigham Young University, Provo, UT84602, USA;Department of Fine Chemistry, Seoul National University of Science & Technology, , Seoul139-743, Republic of Korea
,
Hyo Geun KooDepartment of Chemistry and Biochemistry, Brigham Young University, Provo, UT84602, USA;Department of Fine Chemistry, Seoul National University of Science & Technology, , Seoul139-743, Republic of Korea
,
Seung Pyo JangDepartment of Chemistry and Biochemistry, Brigham Young University, Provo, UT84602, USA;Department of Fine Chemistry, Seoul National University of Science & Technology, , Seoul139-743, Republic of Korea
,
Alan B. ErdmannDepartment of Chemistry and Biochemistry, Brigham Young University, Provo, UT84602, USA
,
Samantha S. VernettiDepartment of Chemistry and Biochemistry, Brigham Young University, Provo, UT84602, USA
,
Cheal KimDepartment of Fine Chemistry, Seoul National University of Science & Technology, , Seoul139-743, Republic of Korea
&
Roger G. HarrisonDepartment of Chemistry and Biochemistry, Brigham Young University, Provo, UT84602, USACorrespondence[email protected]
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Pages 245-250 | Received 03 Jul 2013, Accepted 02 Oct 2013, Published online: 18 Nov 2013
 
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Abstract

The synthesis, spectroscopic characterisation, conformational switching and fluorescence quenching efficiency of a resorcinarene-based cavitand containing Zn-salen (Zn-Cav) are reported. Synthesis of Zn-Cav was accomplished by the condensation of a quinoxaline derivatised with Zn-salen and a resorcinarene-based cavitand containing three quinoxalines. 1H NMR spectroscopy confirmed that in DMSO, chloroform and acetone Zn-Cav resides in the vase conformation. The molecular geometry of Zn-Cav selectively changes from vase to kite under acidic conditions. Detection by fluorescence quenching of nitro-containing molecules, such as 4-nitrotoluene, 2,4-dinitrotoluene and 2,3-dimethyl-2,3-dinitrobutane was explored by spectrofluorimetry. It was found that the fluorescence of Zn-Cav is efficiently quenched by nitroaromatic compounds.

Acknowledgement

We acknowledge Brigham Young University for the financial support and the NSF for instrument funding.

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