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Spirofluorene‐Cored Difluoroboron β‐Diketonate Complexes with Terminal Carbazole: Synthesis, Self‐Assembling, and Fluorescent Sensory Properties
Author(s) -
Zhai Lu,
Shu Yuanhong,
Sun Jingbo,
Sun Meng,
Song Yingying,
Lu Ran
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900161
Subject(s) - chemistry , aniline , methylcyclohexane , carbazole , fluorescence , cyclohexane , molecule , photochemistry , conjugated system , cavitand , polymer chemistry , chromophore , organic chemistry , supramolecular chemistry , toluene , polymer , physics , quantum mechanics
Spirofluorene‐cored bis(difluoroboron β‐diketonate) complexes bearing terminal carbazoles ( CbzBSF ) and tert ‐butylcarbazoles ( TCbzBSF ) have been synthesized. It was found that only TCbzBSF could form organogels in cyclohexane and methylcyclohexane, suggesting that tert ‐butylcarbazole was essential for its organogelation directed by weak π–π interactions. It is worth noting that TCbzBSF could entrap ca. 5800 molecules of methylcyclohexane per gelator molecule, so this fully conjugated complex without traditional gelation group could be considered as a supergelator. The gained organogel showed reversible thixotropic and temperature‐dependent sol‐gel transitions. In particular, the orange red fluorescence of the xerogel‐based film of TCbzBSF could be quenched when exposed to gaseous aromatic amines of aniline, N ‐methylaniline, and N , N ‐dimethylaniline. The detection limit for aniline vapor of the xerogel‐based film was as low as 0.56 ppb.