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Title: New Synthetic Route to Water‐Soluble Prism[5]arene Hosts and Their Molecular Recognition Properties**
Abstract

We report that the direct macrocyclization of naphthalene monomers bearing ethyl ester functional groups delivers prism[5]arene derivatives, which can be deprotected to yield water‐soluble prism[5]arenes (H1andH3).1H NMR spectroscopy showed that dicationic guests bind with the hydrophobic cores buried inside the anisotropic magnetically shielding cavity. Isothermal titration calorimetry measurements showed thatH1andH3are high‐affinity hosts in PBS‐buffered water with Kavalues exceeding 109 M−1for a select guest. The complexation events are driven by the non‐classical hydrophobic effect, CH⋅⋅⋅π interactions, and electrostatic interactions. HostH1displays somewhat higher affinity toward a common guest than pillar[6]arene bearing carboxylic acid functional groups but is significantly less potent than pillar[6]arene bearing sulfate groups.H1andH3should be considered alongside other high affinity hosts for a variety of chemical and biological applications.

 
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Award ID(s):
2105857 2018860
NSF-PAR ID:
10372838
Author(s) / Creator(s):
 ;  
Publisher / Repository:
Wiley Blackwell (John Wiley & Sons)
Date Published:
Journal Name:
Chemistry – A European Journal
Volume:
28
Issue:
56
ISSN:
0947-6539
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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