Square tiling by square macrocycles at the liquid/solid interface: co-crystallisation with one- or two-dimensional order

Chemistry : a European Journal
Kazukuni TaharaYoshito Tobe

Abstract

We have systematically investigated the self-assembled monolayers of seven bimolecular mixtures of square-shaped pyridinophanes and cyclophanes bearing alkoxy or alkoxycarbonyl substituents in the presence of the tropylium ion as a marker of pyridinophanes at liquid/graphite interfaces by means of scanning tunnelling microscopy (STM). The purpose of this work was to elucidate the mixing behaviour of these macrocycles highlighting the formation of one- or two-dimensionally ordered square tilings consisting of alternating alignments of different macrocycles as a result of attractive dipole-dipole or hydrogen-bonding interactions; four co-crystals differing in the dimensionality of the ordering of pyridinophane and cyclophane were observed. The different modes of interaction between the functional groups (ether or carbonyl group) in the side-chains of the pyridinophanes and cyclophanes lead to the formation of co-crystals with dimensionally different orderings of the two macrocycles. These observations revealed that a slight modification of the molecular structure may dramatically change the mixing behaviour and structures of the co-crystals.

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Citations

Jan 18, 2017·Chemical Reviews·Xavier BoujuAndré Gourdon
Oct 28, 2019·Chemistry : a European Journal·Koji Miki, Kouichi Ohe
Oct 3, 2017·Langmuir : the ACS Journal of Surfaces and Colloids·Kohei IritaniYoshito Tobe
May 3, 2018·Langmuir : the ACS Journal of Surfaces and Colloids·Kohei IritaniYoshito Tobe

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