From S,N‐Heteroacene to Large Discotic Polycyclic Aromatic Hydrocarbons (PAHs): Liquid Crystal versus Plastic Crystalline Materials with Tunable Mechanochromic Fluorescence

A novel type of discotic polycyclic aromatic hydrocarbon (PAH) based on an enlarged dibenzo[a,c]phenazine core has been developed. The large conjugated mesogenic core with increased dipole moment derived from S,N heteroatoms facilitates the formation of highly ordered columnar superstructures both i...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-05, Vol.57 (21), p.6161-6165
Main Authors: Yuan, Wei, Ren, Xiang‐Kui, Li, Mengwei, Guo, Hongshuang, Han, Yi, Wu, Mengjiao, Wang, Qi, Li, Miaomiao, Chen, Yulan
Format: Article
Language:English
Subjects:
Bischler–Napieralski cyclization
Dipole moments
Fluorescence
liquid crystal
Liquid crystals
mechanochromic fluorescence
Mechanoluminescence
Mesophase
Phenazine
plastic crystal
Plastics
Polycyclic aromatic hydrocarbons
polycyclic aromatic hydrocarbons (PAHs)
Superstructures
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Summary:A novel type of discotic polycyclic aromatic hydrocarbon (PAH) based on an enlarged dibenzo[a,c]phenazine core has been developed. The large conjugated mesogenic core with increased dipole moment derived from S,N heteroatoms facilitates the formation of highly ordered columnar superstructures both in solution and bulk. Columnar mesophases, including liquid crystal (LC) and plastic crystal (PC) assemblies could form unprecedentedly based on the same PAH core. The cores are delicately modulated by the peripherical alkoxy chains. Both mesogens have mechanochromic fluorescent (MCF) character, which is also structure dependent and correlated with the different mesophase formation. For the first time, MCF properties can be realized in such a large conjugated mesogenic system. PAH core: A new class of discotic polycyclic aromatic hydrocarbon (PAH) mesogens features a π‐extended phenanthroline part. Room‐temperature liquid crystal and plastic crystal assemblies can be obtained from the same PAH core. For the first time, mesophase correlated mechanochromic fluorescence (MCF) was achieved in such a large conjugated system.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201801488