Issue 27, 2014

Guest induced head-to-tail columnar assembly of 5,17-difunctionalized calix[4]arene

Abstract

Calix[4]arene possessing two catechol side arms 1 and organic molecules (nPrOH, AcOH, AcOEt, and CH3CN) crystallized to afford cocrystals: 1·(nPrOH)4, 1·(AcOH)4, 1·(AcOEt), and 1·(CH3CN)2. In these cocrystals, calix[4]arene 1 is arranged one-dimensionally, forming head-to-tail columnar structures. The organic guests settle in the residual space between the columnar structures; they are captured by the catechol side arms through hydrogen bonding. In the cocrystal 1·(H2O)2, a continuous zigzag array of 1 is formed instead of the columnar assembly, demonstrating that the organic guests induced the formation of the head-to-tail columnar structures in the crystal packing. The crystalline apohost 1apo was prepared by the desorption of the MeOH guests from the cocrystal 1·(MeOH)4; this compound adsorbed the MeOH vapour, reconstructing the original crystal packing. When 1apo adsorbed the iPrOH vapour, a cocrystal with a crystal structure similar to that of 1·(MeOH)4 was formed, suggesting that 1apo has a crystal structure similar to that of 1·(MeOH)4.

Graphical abstract: Guest induced head-to-tail columnar assembly of 5,17-difunctionalized calix[4]arene

Supplementary files

Article information

Article type
Paper
Submitted
31 Mac 2014
Accepted
09 Mei 2014
First published
13 Mei 2014

CrystEngComm, 2014,16, 6023-6032

Guest induced head-to-tail columnar assembly of 5,17-difunctionalized calix[4]arene

R. Sekiya, Y. Yamasaki, W. Tada, H. Shio and T. Haino, CrystEngComm, 2014, 16, 6023 DOI: 10.1039/C4CE00667D

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