Synthetic β-Cyclodextrin Dimers for Squaraine Binding: Effect of Host Architecture on Photophysical Properties, Aggregate Formation and Chemical Reactivity

Sauradip Chaudhuri, Molly Verderame, Teresa L. Mako, Y. M.Nuwan D.Y. Bandara, Ashvin I. Fernando, Mindy Levine

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)1964-1974
Number of pages11
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number17
DOIs
StatePublished - 8 May 2018
Externally publishedYes

Keywords

  • Host-guest systems
  • Hydrophobic effect
  • Inclusion compounds
  • Macrocycles
  • Supramolecular chemistry

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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