Colorimetric fluoride sensor based on 1,8-naphthalimide derivatives

Ren, Jing; Wu, Zhen; Zhou, Ying; Li, Yan; Xu, Zuxun

doi:10.1016/j.dyepig.2011.04.012

Cited by 121 publications

(68 citation statements)

References 27 publications

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“…For TBS-NA, the calculated signals at d = 8.8, 8.7, 8.6, 7.7 and 7.0 ppm are assigned to the protons of He, Hb, Hc, Hd and Ha, respectively. This calculation result agrees well with the previous experimental 1 H NMR spectrum (see Table S2) [27] Table S3) instead of Hb shift to upfield while the proton signal of Hc 0 shifts to downfield, which can be ascribed to the electron density redistribution of the p-conjugated framework as a result of the desilylation reaction.…”

Section: 2supporting

confidence: 82%

“…Relaxation of the transition state toward the intermediate and the products by IRC calculations did not detect any intermediates. Thus, the results indicated that the present desilylation reaction belonged to the S N 2 reaction type and had a low reaction barrier (DG = 14.9 kcal/mol) for the Si-O bond cleavage and the formation of NA and SiCH 3 F. Meanwhile, this low-barrier reaction induces the rapid response speed of the chemosensor TBS-NA for fluoride anion [27].…”

Section: Optimized Ground-state Structuresmentioning

confidence: 89%

“…For this aim, we first optimized the geometries of all the complexes formed between TBS-NA and the involved anions in [27]. And such optimizations were performed with DFT/B3LYP/ TZVP and IEF-PCM (MeCN, e = 35.69).…”

Section: Binding Energymentioning

confidence: 99%

“…Recently, a desilylation-reaction-based colorimetric chemosensor for fluoride anion, 4-(tert-butyldimethylsilyloxy)-N-butyl-naphthalimide (TBS-NA), has been reported by Ren and coworkers [27] (see Scheme 1). Like many previously reported ratiometric fluorescent chemosensors based on the fluoride-triggered Si-O cleavage reaction [2,3,6,18,20], the chemosensor TBS-NA also has the potential as a ratiometric fluorescent chemosensor.…”

Section: Introductionmentioning

confidence: 99%

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Intramolecular charge transfer and sensing mechanism for a colorimetric fluoride sensor based on 1,8-naphthalimide derivatives

et al. 2013

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The sensing mechanism of a fluoride colorimetric chemosensor 4-(tert-butyldimethylsilyloxy)-Nbutyl-naphthalimide has been studied with density functional theory and time-dependent density functional theory methods. The theoretical results suggest that the low barrier of the desilylation reaction is responsible for the rapid response speed to the fluoride anion of the chemosensor. The calculated vertical excitation energies in the ground state of the chemosensor and its desilylation product agree well with the experimental UV-Vis absorbance spectra. It is also found that the intramolecular charge transfer process of the first excited state of the desilylation product induces the redshift of the absorbance and fluorescence spectra of the desilylation product compared with that of the chemosensor. Further, the previously experimentally incorrect assignment of the 1 H NMR spectrum of the desilylation product has been rectified in the present theoretical study.

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Section: 2supporting

confidence: 82%

Section: Optimized Ground-state Structuresmentioning

confidence: 89%

Section: Binding Energymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Intramolecular charge transfer and sensing mechanism for a colorimetric fluoride sensor based on 1,8-naphthalimide derivatives

et al. 2013

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“…The desilylation products of the fluorescent chemosensors with TBDMS or TBDPS substituents have been previously reported to be an anionic form in organic solvent. 10,18,20 Notably, the experiment was carried out in tetrahydrofuran (THF). 13 Thus, almost no free hydrogen ions exist in the organic solvent, and the chances of binding these ions with fluoride anions and the desilylation product of DBM to form DBMOHF are small.…”

Section: Introductionmentioning

confidence: 99%

Sensing mechanism for a fluoride chemosensor: invalidity of excited-state proton transfer mechanism

Chen

Zhou

Yang

et al. 2013

Phys. Chem. Chem. Phys.

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Our density functional theory (DFT)/time-dependent DFT calculations for the fluoride anion sensor, 5,7-dibromo-8-tert-butyldimethylsilyloxy-2-methylquinoline (DBM), suggested a different sensing mechanism from the experimentally proposed one (Chem. Commun., 2011, 47, 7098). Instead of the formation of fluoridehydrogen-bond complex (DBMOHF) and excited-state proton transfer mechanism, the theoretical results predicted a sensing mechanism based on desilylation reaction and intramolecular charge transfer (ICT). The fluoride anion reacted with DBM and formed an anion (DBMO), with the ICT causing a red shift in the absorbance and emission spectra of the latter. The calculated vertical excitation energies in the ground and first excited states of both DBM and DBMO, as well as the calculated 1 H NMR spectra, significantly reproduced the experimental measurements, providing additional proofs for our proposed sensing mechanism for DBM.

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A colorimetric and fluorescent probe for fluoride ions based on 6‐acetyl‐2‐naphthol

Hou

Song

2013

Luminescence

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A colorimetric and turn-on fluorescent probe for fluoride ions, tert-butyldimethylsilane 6-acetyl-2-naphtholate, was readily synthesized from 6-acetyl-2-naphthol and tert-butyldimethylchlorosilane (TBSCl). The probe exhibits high sensitivity and good selectivity for fluoride ions in acetonitrile. The inherent mechanism involves the cleavage of the Si-O bond in the probe, which induced yellow color formation and prominent fluorescence enhancement.

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Colorimetric fluoride sensor based on 1,8-naphthalimide derivatives

Cited by 121 publications

References 27 publications

Intramolecular charge transfer and sensing mechanism for a colorimetric fluoride sensor based on 1,8-naphthalimide derivatives

Intramolecular charge transfer and sensing mechanism for a colorimetric fluoride sensor based on 1,8-naphthalimide derivatives

Sensing mechanism for a fluoride chemosensor: invalidity of excited-state proton transfer mechanism

A colorimetric and fluorescent probe for fluoride ions based on 6‐acetyl‐2‐naphthol

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