Synthetic β‐Cyclodextrin Dimers for Squaraine Binding: Effect of Host Architecture on Photophysical Properties, Aggregate Formation and Chemical Reactivity
Reported herein is the synthesis and application of three novel β‐cyclodextrin dimer hosts for the complexation of near infrared (NIR) squaraine dyes in aqueous solution. A series of eight different N‐substituted N‐methyl anilino squaraine dyes with variable terminal groups are investigated, with an...
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Published in | European journal of organic chemistry Vol. 2018; no. 17; pp. 1964 - 1974 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
WEINHEIM
Wiley
08.05.2018
Wiley Subscription Services, Inc |
Subjects | |
Online Access | Get full text |
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Summary: | Reported herein is the synthesis and application of three novel β‐cyclodextrin dimer hosts for the complexation of near infrared (NIR) squaraine dyes in aqueous solution. A series of eight different N‐substituted N‐methyl anilino squaraine dyes with variable terminal groups are investigated, with an optimal n‐hexyl‐substituted squaraine guest demonstrating binding constants orders of magnitude higher than the other squaraine–host combinations and comparable to literature‐reported systems. Moreover, hydrophobic complexation of the squaraine dyes with the β‐cyclodextrin dimer hosts causes drastic changes in the squaraine's photophysical properties, propensity for aggregation and susceptibility to hydrolytic decay.
Three newly synthesized β‐cyclodextrin dimers have been found to complex a variety of squaraine dyes with high association constants and interesting geometries. Displacement of the squaraine dye from the cavity by an analyte provides a promising sensing platform. |
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ISSN: | 1434-193X 1099-0690 |
DOI: | 10.1002/ejoc.201800283 |