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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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2018; no. 17; pp. 1964 - 1974
Main Authors Chaudhuri, Sauradip, Verderame, Molly, Mako, Teresa L., Bandara, Y. M. Nuwan D. Y., Fernando, Ashvin I., Levine, Mindy
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 08.05.2018
Wiley Subscription Services, Inc
Subjects
Binding
Biomimetics
Chemical synthesis
Chemistry
Chemistry, Organic
Complexation
Cyclodextrins
Dimers
Dyes
Host‐guest systems
Hydrophobic effect
Inclusion compounds
Macrocycles
Physical Sciences
Science & Technology
Substitutes
Supramolecular chemistry
TRIMERS
POLYCYCLIC AROMATIC-HYDROCARBONS
Macrocycles
Supramolecular chemistry
Host-guest systems
DEEP
FLUORESCENCE
Inclusion compounds
MOLECULAR RECOGNITION
MACROCYCLE
Hydrophobic effect
CHEMISTRY
ENERGY-TRANSFER
COMPLEXATION
WATER
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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.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201800283