Halogen-Bonding-Driven Self-Assembly of Solvates of Tetrabromoterephthalic Acid
Nucharee Chongboriboon,
Kodchakorn Samakun,
Winya Dungkaew,
Filip Kielar,
Mongkol Sukwattanasinitt,
Kittipong Chainok
Affiliations
Nucharee Chongboriboon
Thammasat University Research Unit in Multifunctional Crystalline Materials and Applications (TU-MCMA), Faculty of Science and Technology, Thammasat University, Pathum Thani 12121, Thailand
Kodchakorn Samakun
Thammasat University Research Unit in Multifunctional Crystalline Materials and Applications (TU-MCMA), Faculty of Science and Technology, Thammasat University, Pathum Thani 12121, Thailand
Winya Dungkaew
Department of Chemistry, Faculty of Science, Mahasarakham University, Mahasarakham 44150, Thailand
Filip Kielar
Department of Chemistry, Faculty of Science, Naresuan University, Phitsanulok 65000, Thailand
Mongkol Sukwattanasinitt
Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
Kittipong Chainok
Thammasat University Research Unit in Multifunctional Crystalline Materials and Applications (TU-MCMA), Faculty of Science and Technology, Thammasat University, Pathum Thani 12121, Thailand
Halogen bonding is one of the most interesting noncovalent attractions capable of self-assembly and recognition processes in both solution and solid phase. In this contribution, we report on the formation of two solvates of tetrabromoterephthalic acid (H2Br4tp) with acetonitrile (MeCN) and methanol (MeOH) viz. H2Br4tp·2MeCN (1MeCN) and H2Br4tp·2MeOH (2MeOH). The host structures of both 1MeCN and 2MeOH are assembled via the occurrence of simultaneous Br···Br, Br···O, and Br···π halogen bonding interactions, existing between the H2Br4tp molecular tectons. Among them, the cooperative effect of the dominant halogen bond in combination with hydrogen bonding interactions gave rise to different supramolecular assemblies, whereas the strength of the halogen bond depends on the type of hydrogen bond between the molecules of H2Br4tp and the solvents. These materials show a reversible release/resorption of solvent molecules accompanied by evident crystallographic phase transitions.
