Single-Atom Tuning of Pyridine-Strapped Pillar[5]arene Capsules for Specific Guest Binding

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-24 DOI:10.1021/acs.orglett.5c00110

Araya Ruengsuk, Sutthipoj Vigromsitdet, Amporn Saekee, Pornnaphat Wichannananon, Tanagorn Sangtawesin, Mongkol Sukwattanasinitt, Jonggol Tantirungrotechai, David J. Harding, Thanthapatra Bunchuay

引用次数: 0

Abstract

Pyridine bis(carboxamide)-strapped pillar[5]arene capsules were synthesized with the serendipitous formation of macrotricyclic products. The structural integrity of the supramolecular capsules, determined by the specific orientation of a single nitrogen atom, controls the electronic properties of the confined binding cavity, facilitating length-selective recognition of aliphatic organic guests with nitrile, isocyanide, and amine functional groups with exceptional host–guest binding affinity and selectivity for 1,2-diaminoethane (K_a > 10⁴ M^–1) in a polar organic solvent.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.