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Reference type: Journal
Authors: Mertz E, Elmer SL, Balija AM, Zimmerman SC
Article Title: Integrating chemosensors for amine-containing compounds into cross-linked dendritic hosts.
Publication date: 2004
Journal: Tetrahedron
Volume: 60
Issue: (49)
Page numbers: 11191-11204.
DOI: 10.1016/j.tet.2004.08.100
Alternative URL: http://www.sciencedirect.com/science/article/B6THR-4DGMYHY-1/2/a357c1f5241535db3ab1fa0d28664297

Abstract: Trifluoroacetylazo dye 1, a known chemosensor for amines, has been integrated into cross-linked dendrimer hosts. Thus, boronic acid 16 was linked to iododye 9 via a Suzuki coupling reaction. In situ deprotection and alkylation with dendrons 3 and 4, containing 8 homoallyl or allyl ether groups, respectively, afforded dendrons 18 and 19 with chemosensor units at their focal point. Conversion of 18 (19) to the bis-imine of butane 1,4-diamine, extensive cross-linking via the ring closing metathesis reaction with Grubbs catalyst 25, and hydrolysis produced dendrimer hosts 28 and 29. Host-guest studies with a small library of amines and alcohols showed 28 and 29 to selectively signal certain diamines but not due to template mediated imprinting


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