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Molecule Recognition and Release Behavior of Naphthalenediimide Derivative via Supramolecular Interactions
Author(s) -
Ma Yudong,
Luo Lixing,
Yang Canglei,
Wang Wei,
Liu Xitong,
Zhang Jing,
Huang Wei
Publication year - 2021
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.202000655
Subject(s) - cocrystal , supramolecular chemistry , perylene , materials science , thermal stability , crystallography , diimide , molecule , crystal engineering , tetracene , crystal (programming language) , pentacene , stereochemistry , chemistry , nanotechnology , crystal structure , hydrogen bond , organic chemistry , computer science , programming language , thin film transistor , layer (electronics)
Self‐assembled charge‐transfer complexes based on supramolecular interactions have attracted immense research interest due to their unique packing and (opto)electronic applications. Herein, two new binary cocrystals with a similar 1:1 mixed‐stack arrangement are synthesized by solvent evaporation or grinding method using N , N ′‐dimethyl‐1,4,5,8‐naphthalene tetracarboxylic diimide (Me‐NDI) as the receptor. Single‐crystal X‐ray diffraction analysis confirms the successful molecular‐level recognition and various weak interaction networks. Upon thermal treatment of 1,4,8,11‐tetramethyl‐6,13‐triethylsilylethynyl pentacene (TMTES‐P)/Me‐NDI complex, in situ cocrystal‐to‐crystal conversion is observed, and the receptor is gradually released, while the perylene/Me‐NDI cocrystal disassembles in the same manner as a single‐component compound. The aligned short‐contact network, good stability of TMTES‐P, and anisotropic attachment energies of the TMTES‐P/Me‐NDI cocrystal disassemble in a manner same to that of a single‐component compound. The aligned short‐contact network, good stability of TMTES‐P, and anisotropic attachment complexes are believed to promote the release of specific molecules. These structure–property relationship results provide new insights into the design of a supramolecular class with desired functionalities in terms of self‐assembled recognition, release, or crystal conversion.