Abstract
Acylhydrazone-based fluorescent conjugated microporous polymers (CMPs) with inter-and intra-hydrogen bonding-controlled emissive properties were prepared. The synthesized CMPs (BH-CMP and ABH-CMP) were characterized by Fourier-transform infrared spectroscopy, X-ray diffraction, solid-state 13C cross polarization/magic angle spinning nuclear magnetic resonance spectroscopy, and photoluminescence spectroscopy. Interestingly, BH-CMP exhibited emission enhancement via adsorption of water molecules, whereas the emission of ABH-CMP, which possesses free amine groups, decreased upon the addition of water molecules. The differences in the emission trends of BH-CMP and ABH-CMP in the presence of water molecules originate from the formation of different hydrogen-bonding networks in each CMP. The acylhydrazone-based CMPs were applied to the detection of nitroaromatic compounds. As a result, ABH-CMP in DMF exhibited high selectivity for 1,3,5-trinitrotoluene (TNT) over other nitroaromatic compounds nitrobenzene, 1-chloro-4-nitrobenzene, 2,3-dichloronitrobenzene, and 2,4-dinitrotoluene.
Highlights
Aggregation-induced emission luminogens (AIEgens) have been intensively applied in optoelectronics such as organic light-emitting diodes (OLEDs) [1,2,3,4,5,6,7], sensors [8,9], and bio-imaging [10,11,12]
We found in our previous work that the emission of the BAH moiety is enhanced by planarization and J-aggregation induced by water-specific polymorphism rather than by the restriction of intramolecular motions (RIM) mechanistic pathway exclusively [19], which led us to introduce the arylacylhydrazone into a conjugated microporous polymers (CMPs) to obtain minimal intramolecular motion
AcOH-catalyzed acylhydrazone-based CMPs were synthesized via the AcOH-catalyzed hydrazone hydrazonereaction formation reaction between 1,3,5-triformylbenzene and terephthalic formation between
Summary
Aggregation-induced emission luminogens (AIEgens) have been intensively applied in optoelectronics such as organic light-emitting diodes (OLEDs) [1,2,3,4,5,6,7], sensors [8,9], and bio-imaging [10,11,12]. The detection of NACs them, hydrazone linkages are effective candidates for the construction of CMP building is essential for the environment and national security because of their explosiveness and blocks with synthetic accessibility toxicity [26,27]. Them, hydrazone linkages are effective candidates for the construction of CMP building They attributed the origin of emission of the acylhydrazone-based COFs to the restriction blocks with synthetic accessibility [35] and stimuli responsiveness [36]. We previously showed that the emission were interested in investigating network polymer systems by introducing acylhydrazone of BAH moieties occurs not by RIR but by planarization and formation of J-aggregates [19]. We studied the effect of the water-induced behaviors of the acylhydrazone-based CMPs, which are in a state of minimal intramolecular hydrogen-bonding motions.
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