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Issue 68, 2015

Crystalline arrays of molecular rotors with TIPS-trityl and phenolic-trityl stators using phenylene, 1,2-difluorophenylene and pyridine rotators

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Abstract

In this work, we describe the synthesis and solid-state characterization of a series of molecular rotors with tri-isopropylsilyloxy-substituted (TIPS) trityl stators axially linked to 1,4-diethynylphenylene, 3,6-diethynyl-1,2-difluorophenylene and 2,5-diethynylpyridine rotators to produce 1,4-bis[(3,3-diphenyl-3-(3′-(tri-isopropylsilyloxy)-phenyl)-prop-1-yn-1-yl)]benzene (1), 1,4-bis[(3,3-diphenyl-3-(3′-(tri-isopropylsilyloxy)-phenyl)-prop-1-yn-1-yl)]-2,3-difluorobenzene (2) and 2,5-bis[(3,3-diphenyl-3-(3′-tri-isopropylsilyloxy)-phenyl)-prop-1-yn-1-yl)]pyridine (3). The subsequent removal of the TIPS protecting group led to their corresponding hydroxyl-substituted trityl derivatives (4) and (5). TIPS- and HO-substituted stators are involved in different inter- and intramolecular interactions (hydrogen bonding, phenyl embraces, C–H–π interactions) that give rise to isomorphic packing motifs that constrained the rotational dynamics in the solid-state to the slow exchange regime.

Graphical abstract: Crystalline arrays of molecular rotors with TIPS-trityl and phenolic-trityl stators using phenylene, 1,2-difluorophenylene and pyridine rotators

Supplementary files

Article information


Submitted
23 Apr 2015
Accepted
15 Jun 2015
First published
15 Jun 2015

RSC Adv., 2015,5, 55201-55208
Article type
Paper
Author version available

Crystalline arrays of molecular rotors with TIPS-trityl and phenolic-trityl stators using phenylene, 1,2-difluorophenylene and pyridine rotators

R. Arcos-Ramos, B. Rodriguez-Molina, E. Gonzalez-Rodriguez, P. I. Ramirez-Montes, M. E. Ochoa, R. Santillan, N. Farfán and M. A. Garcia-Garibay, RSC Adv., 2015, 5, 55201 DOI: 10.1039/C5RA07422C

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