Issue 47, 2014

Cocrystallization of pyrogallol[4]arenes with 1-(2-pyridylazo)-2-naphthol

Abstract

Cocrystallizations of pyrogallol[4]arenes and 1-(2-pyridylazo)-2-naphthol (PAN) are investigated herein in order to determine the effect of aliphatic tail-length and solvent on crystal packing, probe orientation, and pyrogallol[4]arene bowl-shape. It is seen that solvent affects the final ratio of PAN to pyrogallol[4]arene, while aliphatic tail-length influences the crystal packing, C–H⋯π interactions, and overall hydrogen bonding. With an aliphatic tail-length of one carbon atom, there is an atypical bilayer structure. As the aliphatic tail-length increases, the resulting cocrystals have the characteristic bilayer structure as well as an increased number of C–H⋯π interactions and decreased hydrogen bonding with the PAN molecules.

Graphical abstract: Cocrystallization of pyrogallol[4]arenes with 1-(2-pyridylazo)-2-naphthol

Supplementary files

Article information

Article type
Paper
Submitted
27 Aug 2014
Accepted
14 Sep 2014
First published
23 Sep 2014

CrystEngComm, 2014,16, 10760-10773

Author version available

Cocrystallization of pyrogallol[4]arenes with 1-(2-pyridylazo)-2-naphthol

C. R. Pfeiffer, D. A. Fowler, S. Teat and J. L. Atwood, CrystEngComm, 2014, 16, 10760 DOI: 10.1039/C4CE01768D

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