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Concentration-dependent supramolecular self-assembly of A1/A2-asymmetric-difunctionalized pillar[5]arene.

ABSTRACT: A series of A1/A2-bromoalkoxy-and-hydroxy-difunctionalized pillar[5]arenes were synthesized by the removal of the pillar[5]arene-bearing benzyl group using catalytic hydrogenation. The difunctionalized pillar[5]arene bearing 8-bromooctoxy and benzyloxy substituents at the A1/A2 positions formed pseudo[1]rotaxane at low concentration and double-threaded supramolecular dimer at high concentration. The supramolecular self-assembly behavior has been probed with multiple methods including varying (variable) concentration ¹H NMR spectroscopy, diffusion-ordered spectroscopy (DOSY), dynamic light scattering (DLS) measurements, isothermal titration calorimetry (ITC), and single-crystal X-ray analysis.

SUBMITTER: Al-Azemi TF

PROVIDER: S-EPMC8693802 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

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Concentration-dependent supramolecular self-assembly of A1/A2-asymmetric-difunctionalized pillar[5]arene.

Al-Azemi Talal F TF Vinodh Mickey M

RSC advances 20210114 5

A series of A1/A2-bromoalkoxy-and-hydroxy-difunctionalized pillar[5]arenes were synthesized by the removal of the pillar[5]arene-bearing benzyl group using catalytic hydrogenation. The difunctionalized pillar[5]arene bearing 8-bromooctoxy and benzyloxy substituents at the A1/A2 positions formed pseudo[1]rotaxane at low concentration and double-threaded supramolecular dimer at high concentration. The supramolecular self-assembly behavior has been probed with multiple methods including varying (va ...[more]

PMID: 35424224

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