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Remarkable Role of C–I···N Halogen Bonding in Thixotropic ‘Halo’gel Formation

Author:
Bhattacharjee, Subham, Bhattacharya, Santanu
Source:
Langmuir 2016 v.32 no.17 pp. 4270-4277
ISSN:
1520-5827
Subject:
X-ray diffraction, crosslinking, gelation, halogens
Abstract:
Halogen-bonding-induced self-assembly in the solution of equimolar mixtures of certain pyridyl-ended oligo p-phenylenevinylene (OPV)-derivatives with 1,4-diiodotetrafluorobenzene is reported. The mode of self-assembly, that is, cocrystallization, thixotropic gelation, or precipitation, depends strongly on the nature of chains (n-alkyl chains as a function of length or short oxyethylene chain) appended to the OPV-backbone as well as on the cooling rate of the corresponding hot solution. Single-crystal X-ray diffraction studies of the cocrystals reveal the “infinite” chain formation via C–I···N halogen-bonding interactions between the two components. In addition, multiple noncovalent interactions induce cross-links among these halogen-bonded “infinite” chains. Interestingly, the molecular packing in the “Cogel” bearing OPV-derivative with oxyethylene chains is found to be very similar to that of the cocrystal of the same.
Agid:
5774022