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Water‐Assisted Formation of Supramolecular Self‐Assembly Systems Based on Distyrylbenzene Derivative
Author(s) -
Cao Xinhua,
Ding Qianqian,
Li Yiran,
Gao Aiping,
Chang Xueping
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201800446
Subject(s) - solvophobic , stacking , intermolecular force , supramolecular chemistry , molecule , self assembly , chemistry , conjugated system , solubility , fluorescence , absorption (acoustics) , photochemistry , supramolecular assembly , derivative (finance) , crystallography , materials science , organic chemistry , polymer , physics , quantum mechanics , financial economics , economics , composite material
Two new π‐conjugated distyrylbenzene derivatives ( 1O and 1S ) were synthesized and carefully characterized through the reaction between 2‐furaldehyde or 2‐thiophenecarboxaldehyde and p‐phenylenediacetonitrile. Organogels 1O and 1S could be obtained in some mixed solvents through addition of water and further balance the solubility. Compounds 1O and 1S had different self‐assembly behavior even if only the difference of one atom in their molecular structures. Organogels 1O and 1S could emit yellow light with the large red‐shift comparing with that of solution state. The emission properties of compounds 1O and 1S in single molecule and dimmer mode were further verified through theoretical calculation. From the UV‐vis absorption spectra, fluorescence emission spectra, FTIR and XRD experiments results, π‐π stacking interaction and strong intermolecular secondary bonding interaction were the main driving force for organogel formation. The different structure from willow leaf‐shaped structure constructed by micron piece to micron fibers structure could be observed through the self‐assembly of molecules 1O and 1S in mixed solvents which exhibited different degrees of hydrophobicity with contact angles of 92°‐135°. This self‐assembly behavior could be tuned via different atom in terminal group of gelator molecule structure. This research would provide a new sample for designing functional π‐conjugated supramolecular self‐assembly system.