Premium
Long‐Range Self‐Assembly of an Electron‐Deficient Hexaazatrinaphthylene with Out‐of‐Plane Substituents
Author(s) -
Chen YiRu,
Zhang YongYun,
Yeh MingChe,
Luo YingTing,
Ong Chi Wi
Publication year - 2020
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201900593
Subject(s) - chemistry , crystallography , spherulite (polymer physics) , differential scanning calorimetry , steric effects , crystal (programming language) , nucleation , molecule , phase transition , stereochemistry , organic chemistry , condensed matter physics , physics , computer science , thermodynamics , programming language
The unprecedented time‐dependent long‐range supramol‐ecular assembly of electron‐deficient hexaazatrinaphthylene (HATN) core based on peripheral crowding with three out‐of‐plane cyclic ketals is reported. The single‐crystal X‐ray structure of the diethyl derivative provided detailed information as to how four molecules in a repeating unit were packed in order to avoid steric crowding of the out‐of‐plane cyclic ketal side chain, providing locking and fastening for stabilizing the self‐assembled structure. The polarizing optical microscopy (POM) and differential scanning calorimetry (DSC) did not instantaneously show any phase transition upon the cooling process. To our surprise, POM images showed a nucleation of spherulite up to 100 μm after 24 hour later. X‐ray diffraction data further confirmed that these soft crystal formed a hexagonal‐like crystal. The long‐range self‐assembly of the new material showed a slight red shift in the UV‐vis absorption spectra and further substantiated by computational method.