Halogen-Bonding-Driven Self-Assembly of Solvates of Tetrabromoterephthalic Acid
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 (H<sub>2</sub>Br<sub>4</sub...
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MDPI AG
2021-02-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/11/2/198 |
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| author | Nucharee Chongboriboon Kodchakorn Samakun Winya Dungkaew Filip Kielar Mongkol Sukwattanasinitt Kittipong Chainok |
| author_facet | Nucharee Chongboriboon Kodchakorn Samakun Winya Dungkaew Filip Kielar Mongkol Sukwattanasinitt Kittipong Chainok |
| author_sort | Nucharee Chongboriboon |
| collection | DOAJ |
| description | 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 (H<sub>2</sub>Br<sub>4</sub>tp) with acetonitrile (MeCN) and methanol (MeOH) viz. H<sub>2</sub>Br<sub>4</sub>tp·2MeCN (<b>1<sub>MeCN</sub></b>) and H<sub>2</sub>Br<sub>4</sub>tp·2MeOH (<b>2<sub>MeOH</sub></b>). The host structures of both <b>1<sub>MeCN</sub></b> and <b>2<sub>MeOH</sub></b> are assembled via the occurrence of simultaneous Br···Br, Br···O, and Br···π halogen bonding interactions, existing between the H<sub>2</sub>Br<sub>4</sub>tp 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 H<sub>2</sub>Br<sub>4</sub>tp and the solvents. These materials show a reversible release/resorption of solvent molecules accompanied by evident crystallographic phase transitions. |
| first_indexed | 2024-03-09T00:47:54Z |
| format | Article |
| id | doaj.art-b07e7e9e462d4a70ab02c159655844cc |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-09T00:47:54Z |
| publishDate | 2021-02-01 |
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| record_format | Article |
| series | Crystals |
| spelling | doaj.art-b07e7e9e462d4a70ab02c159655844cc2023-12-11T17:26:35ZengMDPI AGCrystals2073-43522021-02-0111219810.3390/cryst11020198Halogen-Bonding-Driven Self-Assembly of Solvates of Tetrabromoterephthalic AcidNucharee Chongboriboon0Kodchakorn Samakun1Winya Dungkaew2Filip Kielar3Mongkol Sukwattanasinitt4Kittipong Chainok5Thammasat University Research Unit in Multifunctional Crystalline Materials and Applications (TU-MCMA), Faculty of Science and Technology, Thammasat University, Pathum Thani 12121, ThailandThammasat University Research Unit in Multifunctional Crystalline Materials and Applications (TU-MCMA), Faculty of Science and Technology, Thammasat University, Pathum Thani 12121, ThailandDepartment of Chemistry, Faculty of Science, Mahasarakham University, Mahasarakham 44150, ThailandDepartment of Chemistry, Faculty of Science, Naresuan University, Phitsanulok 65000, ThailandDepartment of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, ThailandThammasat University Research Unit in Multifunctional Crystalline Materials and Applications (TU-MCMA), Faculty of Science and Technology, Thammasat University, Pathum Thani 12121, ThailandHalogen 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 (H<sub>2</sub>Br<sub>4</sub>tp) with acetonitrile (MeCN) and methanol (MeOH) viz. H<sub>2</sub>Br<sub>4</sub>tp·2MeCN (<b>1<sub>MeCN</sub></b>) and H<sub>2</sub>Br<sub>4</sub>tp·2MeOH (<b>2<sub>MeOH</sub></b>). The host structures of both <b>1<sub>MeCN</sub></b> and <b>2<sub>MeOH</sub></b> are assembled via the occurrence of simultaneous Br···Br, Br···O, and Br···π halogen bonding interactions, existing between the H<sub>2</sub>Br<sub>4</sub>tp 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 H<sub>2</sub>Br<sub>4</sub>tp and the solvents. These materials show a reversible release/resorption of solvent molecules accompanied by evident crystallographic phase transitions.https://www.mdpi.com/2073-4352/11/2/198halogen bondshydrogen bondssolvatestructural phase transitionHirschfeld surfacetetrabromoterephthalic acid |
| spellingShingle | Nucharee Chongboriboon Kodchakorn Samakun Winya Dungkaew Filip Kielar Mongkol Sukwattanasinitt Kittipong Chainok Halogen-Bonding-Driven Self-Assembly of Solvates of Tetrabromoterephthalic Acid Crystals halogen bonds hydrogen bonds solvate structural phase transition Hirschfeld surface tetrabromoterephthalic acid |
| title | Halogen-Bonding-Driven Self-Assembly of Solvates of Tetrabromoterephthalic Acid |
| title_full | Halogen-Bonding-Driven Self-Assembly of Solvates of Tetrabromoterephthalic Acid |
| title_fullStr | Halogen-Bonding-Driven Self-Assembly of Solvates of Tetrabromoterephthalic Acid |
| title_full_unstemmed | Halogen-Bonding-Driven Self-Assembly of Solvates of Tetrabromoterephthalic Acid |
| title_short | Halogen-Bonding-Driven Self-Assembly of Solvates of Tetrabromoterephthalic Acid |
| title_sort | halogen bonding driven self assembly of solvates of tetrabromoterephthalic acid |
| topic | halogen bonds hydrogen bonds solvate structural phase transition Hirschfeld surface tetrabromoterephthalic acid |
| url | https://www.mdpi.com/2073-4352/11/2/198 |
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