Bis-naphthalimide-based supramolecular self-assembly system for selective and colorimetric detection of oxalyl chloride and phosgene in solution and gas phase

Two bis-naphthalimide-based supramolecular gelators (NN-3 and NN-4) with a little difference of position of amino groups were designed and synthesized for the detection of oxaloyl chloride and phosgene. Energy transfer could be occurred between two naphthalimide groups in molecules NN-3 and NN-4. Ye...

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Bibliographic Details
Published in:Chinese chemical letters 2023-06, Vol.34 (6), p.107644-496, Article 107644
Main Authors: Wang, Qingqing, Wu, Huijuan, Gao, Aiping, Ge, Xuefei, Chang, Xueping, Cao, Xinhua
Format: Article
Language:English
Subjects:
Bis-naphthalimide
Colorimetric detection
Multi-modes
Self-assembly
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Summary:Two bis-naphthalimide-based supramolecular gelators (NN-3 and NN-4) with a little difference of position of amino groups were designed and synthesized for the detection of oxaloyl chloride and phosgene. Energy transfer could be occurred between two naphthalimide groups in molecules NN-3 and NN-4. Yellow gels NN-3 and NN-4 were formed in some mixed solvents, and nanofibers with different size were obtained in these gels. The self-assembly processes of NN-3 and NN-4 in different solvents were investigated by UV-vis absorption, fluorescent spectra, SEM, FTIR, XRD and NMR. Gelators NN-3 and NN-4 could selectively detect oxaloyl chloride in solution and film states, but detect phosgene only in solution. NN-3 exhibited the ratiometric detection ability towards oxaloyl chloride and phosgene with the low limit of detection (LOD) of 210 nmol/L and 90 nmol/L, respectively. NN-4 as the corresponding control sample, it owned the higher LOD towards oxaloyl chloride and phosgene of 12.4 µmol/L and 64 µmol/L, respectively. Interestingly, films NN-3 and NN-4 could sensitively detect oxaloyl chloride gases with the low LOD of 2.0 ppm and 8.34 ppm, respectively. The detection mechanisms of NN-3 and NN-4 were well studied by 1H NMR titration, HRMS and theoretical calculation. Bis-naphthalimide-based gelator with intramolecular energy transfer was designed and synthesized. This supramolecular self-assembly system had the selective and colorimetric detection performance to oxalyl chloride and phosgene in solution and gas phase. [Display omitted]
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2022.06.067