Open AccessCo‐Crystal Formation of Partially Fluorinated 1,3,5‐Tris(phenylethynyl)benzenes
Author(s) -
Weddeling JanHenrik,
Waltersmann Paul Lukas,
Neumann Beate,
Stammler HansGeorg,
Mitzel Norbert W.
Publication year - 2021
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.202100194
Subject(s) - intermolecular force , aryl , chemistry , crystallization , sonogashira coupling , melting point , crystal (programming language) , crystallography , tris , crystal structure , molecule , palladium , organic chemistry , catalysis , alkyl , biochemistry , computer science , programming language
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.