Effect of a Bromine Substituent on the Self-Assembly of an Oligopyridine at the Liquid|Solid Interface
2020
Goll, Felix D. | Schleper, A Lennart | Kuehne, Alexander J. C. | Ziener, Ulrich
Synthesis and self-assembly of the first halogenated bis(terpyridine) (BTP) show that 2,4′-BTPBr forms two different morphologies at the solution|highly oriented pyrolytic graphite (HOPG) interface when deposited from 1,2,4-trichlorobenzene (TCB). 2,4′-BTPBr self-assembles either in a rectangular or an oblique unit cell, strongly deviating from the assembly behavior of the parent compound 2,4′-BTP. High-resolution images and energy considerations reveal that no halogen bonds are present. Instead, rather weak hydrogen bonds C–H···N are responsible for the adopted two-dimensional (2D) structures. Co-deposition of the brominated species with 2,4′-BTP results in phase separation, pointing to a highly expressed self-recognition process. This selectivity is based on a specific hydrogen bonding pattern and a minimization of the dipole moment.
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