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DOI: 10.1055/s-2008-1078685
Hg²+-Gated Molecular Switch
Contributor(s):Timothy M. Swager, Jeewoo LimInstitute of Chemistry, Chinese Academy of Sciences and Graduate School of Chinese Academy of Sciences, Beijing, P. R. of China
An Hg²+-Gated Chiral Molecular Switch Created by Using Binaphthalene Molecules with Two Anthracene Units and Two 1,3-Dithiole-2-thione (1,3-Dithiole-2-one) Units
Chem. Eur. J. 2008, 14: 5680-5686
Publication History
Publication Date:
22 August 2008 (online)
Key words
molecular switches - anthracene - binaphthalene
Significance
The authors report a synthesis of a molecular switch in which photoreactivity at one site of the molecule can be regulated by functionalization of a remote site within the same molecule. The report illustrates the principle of controlling reactivity at one position of a molecule by changes at a different, remote position.
Comment
The authors have previously discovered that, while 1,3-dithiole-2-thione can quench the excited state of anthracene, 1,3-dithiole-2-one cannot, which is consistent with the observation that 3 is strongly fluorescent and 2 is only weakly fluorescent. While the anthracene groups of 2 do not undergo photo-induced dimerization, the reaction occurs readily in the presence of Hg²+, which converts 2 into 3.