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A Smart Phase‐Selective Gelator for Recycling Aromatic Solvents, the Removal of Toxic Dyes, and Molecular Delivery
Author(s) -
Ran Xia,
Li Yajie,
Gao Qiongqiong,
Qiu Weihong,
Guo Lijun
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600480
Subject(s) - chemistry , phase (matter) , organic chemistry , nanotechnology , combinatorial chemistry , materials science
The phase‐selective gelation properties of a low‐molecular‐mass organogelator, N ‐(3,4,5‐tributoxyphenyl)‐ N ′‐4‐[(4‐hydroxyphenyl)azophenyl] benzohydrazide (BNB‐t4), and its applications in recycling aromatic solvents, removing toxic dyes, and molecular delivery, are reported. The hydroxy head group, hydrazide group, and three butyl chains in this compound provide the collective driving force for self‐assembly and make BNB‐t4 an excellent phase‐selective gelator (PSG). FTIR and UV/Vis spectroscopy suggest that the driving forces for the gelation are hydrogen‐bonding, π–π stacking and Van der Waals interactions. The critical gelation concentration (CGC) of BNB‐t4 in aromatic solvents is very low (e.g., 0.6 mg mL −1 in toluene), which suggests that the BNB‐t4 PSG could extract aromatic solvents from aqueous mixtures. Our results indicate that the entangled fibrous network and its rheological properties enable BNB‐t4 to function as a reversible material for removing toxic dyes from aqueous solution with efficiencies as high as 97 %. Furthermore, its combined phase‐selection and reversible phase‐transition properties confer BNB‐t4 the ability to absorb and release organic compounds with efficiencies of up to 98 %. Taken together, these results demonstrate that BNB‐t4 could be used to construct smart materials for environment remediation and molecular delivery.