A Schiff base-based ratiometric chemosensor conjugated NBD derivative with the large Stokes shift for formaldehyde detection

Wechakorn, Kanokorn; Supalang, Saichon; Suanpai, Supattra

doi:10.1016/j.tet.2020.131411

Cited by 11 publications

(10 citation statements)

References 36 publications

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“…This new solution then exhibited a peak at 582 nm, whereas the intensity of the peak at 475 nm was reduced ( Figures 17 and 18 ). 39 The former probe has a lower LOD with 30 μM (0.03 M) than the CHA probe (0.20 M). 40 …”

Section: Organic Chemosensorsmentioning

confidence: 93%

“…Upon the addition of FA, the color of the solution transitioned from yellow to deep purple. This new solution then exhibited a peak at 582 nm, whereas the intensity of the peak at 475 nm was reduced (Figures and ) . The former probe has a lower LOD with 30 μM (0.03 M) than the CHA probe (0.20 M) …”

Section: Organic Chemosensorsmentioning

confidence: 99%

“…According to the above mechanism, Wechakorn et al. 39 worked on an N 1 -(7-nitrobenzo[c][1,2,5]oxadiazol-4yl) benzene-1,2-diamine sensor for FA detection. The absorption spectrum showed a peak at 475 nm.…”

Section: Organic Chemosensorsmentioning

confidence: 99%

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Recent Progress in the Development of Organic Chemosensors for Formaldehyde Detection

et al. 2023

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Formaldehyde has become a prominent topic of interest because of its simple molecular structure, release from various compounds in the near vicinity of humans, and associated hazards. Thus, several researchers designed sophisticated instrumentations for formaldehyde detection that exhibit real-time sensing properties and are cost-effective and portable with high detection limits. On these grounds, this review is centered on an analysis of optical chemosensors for formaldehyde that specifically fall under the broad spectrum of organic probes. In this case, this review discusses different organic functionalities, including amines, imines, aromatic pillar arenes, β-ketoesters, and β-diketones, taking part in various reaction mechanisms ranging from aza-Cope rearrangement and Schiff base and Hanztch reactions to aldimine condensation. In addition, this review distinguishes reaction mechanisms according to photophysical phenomena, that is, aggregation-induced emission, photoinduced electron transfer, and intramolecular charge transfer. Furthermore, it addresses the instrumentation involved in gas-based and liquid formaldehyde detection. Finally, it discusses the gaps in existing technologies followed by a succinct set of recommendations for future research.

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Section: Organic Chemosensorsmentioning

confidence: 93%

Section: Organic Chemosensorsmentioning

confidence: 99%

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Recent Progress in the Development of Organic Chemosensors for Formaldehyde Detection

et al. 2023

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“…This issue motivates the development of opticali maging technologyf or FA detection. Newly developed FA detection methods such as electrochemical, [9] colorimetrica pproaches, [10] and fluorescentp robes [11] have strongs pecificity, high sensitivity,a nd selectivity advantages. These methods can also monitor reactive carbonyl substances in living systems and have broad application prospects.…”

Section: Introductionmentioning

confidence: 99%

Mechanistic Investigation on Chemiluminescent Formaldehyde Probes

Yue

et al. 2021

Chemistry A European J

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Af irst-generation pair of chemiluminescentf ormaldehyde (FA) probes (CFAP540a nd CFAP700)w as reported recently.C FAP540 and CFAP700, with high selectivity and sensitivity to FA,a re, respectively,s uitable in cell and in vivo. Experimentalists have confirmed that both probes utilize a general2-aza-Cope FA-reactivet rigger and ac hemiluminogenic phenoxydioxetane scaffold. The mechanism and detailed process of CFAP chemiluminescence (CL) remainlargely unknown. In the present paper,(time-dependent) density functional theory calculations are performed on the entire reactionp rocess of CFAP540 with FA to produce CL. The calculations elucidated the CL-producingp rocess:F Ai nitiates the decomposition of CFAP540 by dehydration condensation, and ap henoxy 1,2-dioxetane is formed through a serieso fr eactions of aza-Cope rearrangement, hydrolysis of imine,a nd b-eliminationo fa lkoxyl group. Afterwards, the produced phenoxy 1,2-dioxetaned ecomposest op roduce the m-oxybenzoate derivativeint he first singlet state (S 1)v ia two crossingsb etween potential energy surfaces of the ground state (S 0)a nd S 1 state. This m-oxybenzoate derivative was assigned as the light emitter of the CFAP540 CL. The CL-producing process and assignment of the light emitter of CFAP700 CL are similar with the corresponding ones of CFAP540. By analyzing the D-p-A architecture of the light emitterso fC FAP540 and CFAP700,aseries of CFAPs is theoreticallyd esigned and as cheme to modulate their CL from visiblet on ear-infrared regioni sp roposedb ya djusting the lengtha nd structure of the p-bridge.

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“…Nowadays, the research developments for selective detection of FA have been focused on two reaction types involving Schiff base (amine and hydrazine) and 2-aza-Cope rearrangement reactions (Scheme 1). [12][13][14][15] These two main approaches are highly selective and sensitive to FA but the 2-aza-Cope reaction basedapproach showed much longer detection time than the Schiff base reaction (Table S1, ESI †). 12 Thus, it is still challenging to develop uorescent probes based on 2-aza-Cope rearrangement with fast detection time.…”

mentioning

confidence: 99%

Quinolizinium-based fluorescent probes for formaldehyde detection in aqueous solution, serum, and test strip via 2-aza-Cope rearrangement

et al. 2022

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A Schiff base-based ratiometric chemosensor conjugated NBD derivative with the large Stokes shift for formaldehyde detection

Cited by 11 publications

References 36 publications

Recent Progress in the Development of Organic Chemosensors for Formaldehyde Detection

Recent Progress in the Development of Organic Chemosensors for Formaldehyde Detection

Mechanistic Investigation on Chemiluminescent Formaldehyde Probes

Quinolizinium-based fluorescent probes for formaldehyde detection in aqueous solution, serum, and test strip via 2-aza-Cope rearrangement

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