Experimental and theoretical investigation of intramolecular cooperativity in cyclic benzene trimer motif.

ABSTRACT: A series of new symmetrical tripodal molecules 1a-4b with a central benzene scaffold substituted with methyl/ethyl groups and three benzimidazolyl units having a bithiophene/biphenyl/5-alkylthiophene motif at the 2-position via a -CH₂- unit were synthesized and characterized by elemental analysis, HR-MS, and NMR spectroscopy. NMR spectral data reveal that all molecules adopt a cyclic benzene trimer (CBT) using three benzimidazolyl units. Intramolecular cooperative edge-to-face C-H⋯π interactions stabilize the CBT motif in solution and are strong in ethyl substituted molecules (1b-4b) compared to methyl substituted (1a-4a) ones. However, the strength of the CBT unit in the tripodal molecule is independent of the length of the substituent at the 2-position of the benzimidaz

SUBMITTER: Kumar CK 

PROVIDER: S-EPMC9059549 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature