Acyclic Cucurbit[n]uril-Type Receptors: Aromatic Wall Extension Enhances Binding Affinity, Delivers Helical Chirality, and Enables Fluorescence Sensing.
Chemistry
; 26(66): 15249-15258, 2020 Nov 26.
Article
em En
| MEDLINE
| ID: mdl-32658342
ABSTRACT
We report the linear extension from M1 to M2 to anthracene walled M3 which adopts a helical conformation (X-ray) to avoid unfavorable interactions between sidewalls. M3 is water soluble (=30â
mm) and displays enhanced optical properties (ϵ=1.28×105 m-1 cm-1 , λmax =370â
nm) relative to M2. The binding properties of M3 toward guests 1-29 were examined by 1 Hâ
NMR and ITC. The M3â
guest complexes are stronger than the analogous complexes of M2 and M1. The enhanced binding of M3 toward neuromuscular blockers 25, 27-29 suggests that M3 holds significant promise as an in vivo reversal agent. The changes in fluorescence observed for M3â
guest complexes are a function of the relative orientation of the anthracene sidewalls, guest concentration, Ka , and guest electronics which rendered M3 a superb component of a fluorescence sensing array. The work establishes M3 as a next generation sequestering agent and a versatile component of fluorescence sensors.
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2020
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Article