Co‐Crystal Formation of Partially Fluorinated 1,3,5‐Tris(phenylethynyl)benzenes
Abstract Several rigid 1,3,5‐tris(phenylethynyl)benzenes with different fluorination patterns were synthesized through selective Sonogashira‐Hagihara coupling reactions to analyze the packing behavior in solid‐state structures. The aggregation is dominated by various intermolecular interactions betw...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Wiley-VCH
2021-10-01
|
| Series: | ChemistryOpen |
| Subjects: | |
| Online Access: | https://doi.org/10.1002/open.202100194 |
| _version_ | 1828958688527777792 |
|---|---|
| author | Dr. Jan‐Henrik Weddeling Paul Lukas Waltersmann Beate Neumann Dr. Hans‐Georg Stammler Prof. Dr. Norbert W. Mitzel |
| author_facet | Dr. Jan‐Henrik Weddeling Paul Lukas Waltersmann Beate Neumann Dr. Hans‐Georg Stammler Prof. Dr. Norbert W. Mitzel |
| author_sort | Dr. Jan‐Henrik Weddeling |
| collection | DOAJ |
| description | Abstract Several rigid 1,3,5‐tris(phenylethynyl)benzenes with different fluorination patterns were synthesized through selective Sonogashira‐Hagihara coupling reactions to analyze the packing behavior in solid‐state structures. The aggregation is dominated by various intermolecular interactions between aryl substituents, triple bonds, C−H bonds and H⋅⋅⋅F contacts. Co‐crystallization experiments for the analysis of preferred aryl‐aryl‐interactions led to 1 : 1 complexes. Intermolecular phenyl‐perfluorophenyl interactions with short centroid‐centroid distances are dominating these co‐crystal structures. They lead to melting point increases of up to 49 °C for the co‐crystals compared to the pure substances. |
| first_indexed | 2024-12-14T08:53:20Z |
| format | Article |
| id | doaj.art-712137e3fb3a4435b942217d8f226116 |
| institution | Directory Open Access Journal |
| issn | 2191-1363 |
| language | English |
| last_indexed | 2024-12-14T08:53:20Z |
| publishDate | 2021-10-01 |
| publisher | Wiley-VCH |
| record_format | Article |
| series | ChemistryOpen |
| spelling | doaj.art-712137e3fb3a4435b942217d8f2261162022-12-21T23:09:00ZengWiley-VCHChemistryOpen2191-13632021-10-0110101059106610.1002/open.202100194Co‐Crystal Formation of Partially Fluorinated 1,3,5‐Tris(phenylethynyl)benzenesDr. Jan‐Henrik Weddeling0Paul Lukas Waltersmann1Beate Neumann2Dr. Hans‐Georg Stammler3Prof. Dr. Norbert W. Mitzel4Lehrstuhl für Anorganische Chemie und Strukturchemie, Centrum für Molekulare Materialien CM2 Fakultät für Chemie Universität Bielefeld Universitätsstraße 25 33615 Bielefeld GermanyLehrstuhl für Anorganische Chemie und Strukturchemie, Centrum für Molekulare Materialien CM2 Fakultät für Chemie Universität Bielefeld Universitätsstraße 25 33615 Bielefeld GermanyLehrstuhl für Anorganische Chemie und Strukturchemie, Centrum für Molekulare Materialien CM2 Fakultät für Chemie Universität Bielefeld Universitätsstraße 25 33615 Bielefeld GermanyLehrstuhl für Anorganische Chemie und Strukturchemie, Centrum für Molekulare Materialien CM2 Fakultät für Chemie Universität Bielefeld Universitätsstraße 25 33615 Bielefeld GermanyLehrstuhl für Anorganische Chemie und Strukturchemie, Centrum für Molekulare Materialien CM2 Fakultät für Chemie Universität Bielefeld Universitätsstraße 25 33615 Bielefeld GermanyAbstract Several rigid 1,3,5‐tris(phenylethynyl)benzenes with different fluorination patterns were synthesized through selective Sonogashira‐Hagihara coupling reactions to analyze the packing behavior in solid‐state structures. The aggregation is dominated by various intermolecular interactions between aryl substituents, triple bonds, C−H bonds and H⋅⋅⋅F contacts. Co‐crystallization experiments for the analysis of preferred aryl‐aryl‐interactions led to 1 : 1 complexes. Intermolecular phenyl‐perfluorophenyl interactions with short centroid‐centroid distances are dominating these co‐crystal structures. They lead to melting point increases of up to 49 °C for the co‐crystals compared to the pure substances.https://doi.org/10.1002/open.2021001941,3,5-triethynylbenzenecrystal engineeringhalogenated arenesphenyl-perfluorophenyl interactionssolid-state structures |
| spellingShingle | Dr. Jan‐Henrik Weddeling Paul Lukas Waltersmann Beate Neumann Dr. Hans‐Georg Stammler Prof. Dr. Norbert W. Mitzel Co‐Crystal Formation of Partially Fluorinated 1,3,5‐Tris(phenylethynyl)benzenes ChemistryOpen 1,3,5-triethynylbenzene crystal engineering halogenated arenes phenyl-perfluorophenyl interactions solid-state structures |
| title | Co‐Crystal Formation of Partially Fluorinated 1,3,5‐Tris(phenylethynyl)benzenes |
| title_full | Co‐Crystal Formation of Partially Fluorinated 1,3,5‐Tris(phenylethynyl)benzenes |
| title_fullStr | Co‐Crystal Formation of Partially Fluorinated 1,3,5‐Tris(phenylethynyl)benzenes |
| title_full_unstemmed | Co‐Crystal Formation of Partially Fluorinated 1,3,5‐Tris(phenylethynyl)benzenes |
| title_short | Co‐Crystal Formation of Partially Fluorinated 1,3,5‐Tris(phenylethynyl)benzenes |
| title_sort | co crystal formation of partially fluorinated 1 3 5 tris phenylethynyl benzenes |
| topic | 1,3,5-triethynylbenzene crystal engineering halogenated arenes phenyl-perfluorophenyl interactions solid-state structures |
| url | https://doi.org/10.1002/open.202100194 |
| work_keys_str_mv | AT drjanhenrikweddeling cocrystalformationofpartiallyfluorinated135trisphenylethynylbenzenes AT paullukaswaltersmann cocrystalformationofpartiallyfluorinated135trisphenylethynylbenzenes AT beateneumann cocrystalformationofpartiallyfluorinated135trisphenylethynylbenzenes AT drhansgeorgstammler cocrystalformationofpartiallyfluorinated135trisphenylethynylbenzenes AT profdrnorbertwmitzel cocrystalformationofpartiallyfluorinated135trisphenylethynylbenzenes |