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Synfacts 2009(2): 0160-0160  
DOI: 10.1055/s-0028-1087503
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

DNA-Assisted Long-Lived Excimer Formation in a Cyclophane

Contributor(s): Timothy M. Swager, Fei Wang
P. P. Neelakandan, D. Ramaiah*
National Institute for Interdisciplinary Science and Technology, Trivandrum, India
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Publication History

Publication Date:
22 January 2009 (online)

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Significance

Reported is a novel water-soluble symmetrical cyclophane 3 that shows intramolecular excimer emission in aqueous medium. In contrast, only locally excited state emissions were observed with 3 in methanol and acetonitrile, or with a model compound 4 in methanol, acetonitrile and water. The uniqueness of 3 is that it undergoes sequence-selective interactions with DNA, showing a bathochromic-shifted emission at 570 nm with elongated lifetime (143.1 s) and significant intensity enhancement, which makes it a promising ”turn-on" DNA sensor.