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J Org Chem. 2013 Mar 1;78(5):1768-77. doi: 10.1021/jo3009897. Epub 2012 Jul 23.

Inclusion compound based approach to arrays of artificial dipolar molecular rotors: bulk inclusions.

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1
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309, United States.

Abstract

We examine the insertion of two dipolar molecular rotors as guests into a host, tris(o-phenylenedioxy)cyclotriphosphazine (TPP, 1), using differential scanning calorimetry, solid-state NMR, powder X-ray diffraction, and dielectric spectroscopy. The rotors are 1-(4'-n-pentylbiphenyl-4-yl)-12-(2,3-dichlorophenyl)-p-dicarba-closo-dodecaborane and 1,12-bis(2,3-dichlorophenyl)-p-dicarba-closo-dodecaborane. Both enter the bulk even though their nominal diameter exceeds the nominal channel diameter and although a closely related rotor, 1-n-hexadecyl-12-(2,3-dichlorophenyl)-p-dicarba-closo-dodecaborane, is known to produce a surface inclusion compound. Rotational barriers of 5.4-9.3 kcal/mol were found for the dichlorophenyl rotator contained within the TPP channel. Clearly, van der Waals diameters in themselves do not suffice to predict TPP channel entry. It is suggested that the efficacy of the p-carborane stopper is reduced by the presence of the two relatively bulky adjacent benzene rings, which help to stretch the channel, and by the axial direction of its axis, which prevents the attached rotator from contributing to the stopping action.

PMID:
22780697
DOI:
10.1021/jo3009897
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