TY - JOUR
T1 - Synthetic β-Cyclodextrin Dimers for Squaraine Binding
T2 - Effect of Host Architecture on Photophysical Properties, Aggregate Formation and Chemical Reactivity
AU - Chaudhuri, Sauradip
AU - Verderame, Molly
AU - Mako, Teresa L.
AU - Bandara, Y. M.Nuwan D.Y.
AU - Fernando, Ashvin I.
AU - Levine, Mindy
N1 - Publisher Copyright:
© 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/5/8
Y1 - 2018/5/8
N2 - 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.
AB - 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.
KW - Host-guest systems
KW - Hydrophobic effect
KW - Inclusion compounds
KW - Macrocycles
KW - Supramolecular chemistry
UR - http://www.scopus.com/inward/record.url?scp=85046549309&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201800283
DO - 10.1002/ejoc.201800283
M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???
AN - SCOPUS:85046549309
SN - 1434-193X
VL - 2018
SP - 1964
EP - 1974
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 17
ER -