We report the formation of highly-ordered self-assembled monolayers of an achiral organic semiconductor molecule. STM results show spontaneous formation of very large single domains of ordered chiral monolayers. DFT calculations support the identification of halogen bonds as the primary interactions that steer molecular self-assembly, leading to organizational chirality.

The title compound, C18H25BrO, crystallized as a racemate with four independent mol-ecules in the asymmetric unit. In the crystal, three of these four mol-ecules are linked via C-Br⋯Br-C halogen bonds [Br⋯Br = 3.662 (2) and 3.652 (2) Å], forming dimers.

P.09.05.7 Acta Cryst. (2005). A61, C362 M–XX'–C Halogen Bonds as Efficient and Reliable Supramolecular Synthons in Organic-inorganic Crystals Fiorenzo Zordan, Lee Brammer, Paul Sherwood, Department of Chemistry, University of Sheffield, Sheffield S3 7HF, UK. Computational Science and Engineering Department, CCLRC Daresbury Laboratory, Daresbury, Warrington WA4 4AD, UK. Email: lee.brammer@sheffi...

The title dihaloaniline, C(6)H(5)ClIN, shows no significant hydrogen bonds nor the commonly observed I⋯I inter-actions in the crystal structure, although an amino group and an I atom are available for such contacts. The crystal structure is stabilized by weak inter-actions involving the amine functionality as donor group and N or halogen atoms as acceptors.

Here we report the use of 10-phenylphenothiazine (PTH) as an inexpensive, highly reducing metal-free photocatalyst for the reduction of carbon-halogen bonds via the trapping of carbon-centered radical intermediates with a mild hydrogen atom donor. Dehalogenations were carried out on various substrates with excellent yields at room temperature in the presence of air.

Intermolecular structures of porous two-dimensional supramolecular networks are studied using scanning tunnelling microscopy combined with density functional theory calculations. The local configurations of halogen bonds in polymorphic porous supramolecular networks are directly visualized in support of previous bulk crystal studies.

Affinity materials based on halogen bonds turned out to be a powerful tool for the molecular recognition of acetone or related carbonyl compounds in the presence of ubiquitous protic molecules. The superior selectivity and sensitivity were found by the gravimetric detection of volatile organic compounds by quartz crystal microbalances.