Multi-state amine sensing by electron transfers in a BODIPY probe

VanDenburgh, Katherine L.; Liu, Yun; Sadhukhan, Tumpa; Benson, Christopher R.; Cox, Natalie; Erbaş-Çakmak, Sündüs; Qiao, Bo; Gao, Xinfeng; Pink, Maren; Raghavachari, Krishnan; Flood, Amar H.

doi:10.1039/c9ob02466b

Cited by 20 publications

(10 citation statements)

References 63 publications

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“…Sensors for detecting volatile compounds are in high demand nowadays once some of them can present toxicity. − This is the case of volatile amines, which are widely used in pharmaceutical and chemical industries and can cause severe injuries such as eye and skin irritation and tearing. , In addition to the toxicity concerns, the monitoring of volatile amine emissions is important for food and beverage quality determination. , In particular, biogenic amine formation in food products is a robust indicator of the quality and state of preservation . Biogenic amines are generally present in low concentrations and are natural metabolic compounds in a number of food products.…”

Section: Introductionmentioning

confidence: 99%

“…1−3 This is the case of volatile amines, which are widely used in pharmaceutical and chemical industries and can cause severe injuries such as eye and skin irritation and tearing. 4,5 In addition to the toxicity concerns, the monitoring of volatile amine emissions is important for food and beverage quality determination. 6,7 In particular, biogenic amine formation in food products is a robust indicator of the quality and state of preservation.…”

Section: ■ Introductionmentioning

confidence: 99%

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Wireless Tags with Hybrid Nanomaterials for Volatile Amine Detection

et al. 2021

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Quality control in the production and processing of raw meat is currently one of the biggest concerns for food industry and would benefit from portable and wireless sensors capable of detecting the onset of spoilage. Raw meat is a natural source of biogenic and volatile amines as byproducts of decarboxylation reactions, and the levels of these compounds can be utilized as quality control parameters. We report herein a hybrid chemiresistor sensor based on inorganic nanofibers of SiO 2 :ZnO (an n-type material) and single-walled carbon nanotubes functionalized with 3,5-dinitrophenyls (a p-type material) with dosimetric sensitivity ∼40 times higher for amines than for other volatile organic compounds, which also provides excellent selectivity. The hybrid nanomaterial-based chemiresistor sensory material was used to convert radio-frequency identification tags into chemically actuated resonant devices, which constitute wireless sensors that can be potentially employed in packaging to report on the quality of meat. Specifically, the as-developed wireless tags report on cumulative amine exposure inside the meat package, showing a decrease in radio-frequency signals to the point wherein the sensor ceased to be smartphone-readable. These hybrid material-modified wireless tags offer a path to scalable, affordable, portable, and wireless chemical sensor technology for food quality monitoring without the need to open the packaging.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Wireless Tags with Hybrid Nanomaterials for Volatile Amine Detection

et al. 2021

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“…[63] An armory of small molecules was also effectively used in AA sensing. Ranging from BODIPY fluorophores, [64] zinc-based Schiff base complex, [65] trifluoroacetophenone-based dyes, [66] certain diarylethenes, [67] aminonaphthalene anhydrides, [68] perylene derivatives, [69] extended distyrylbenzenes [70] to bio-inspired diatoms derived from algae [71] were used to detect AA efficiently.…”

Section: Introductionmentioning

confidence: 99%

A New Compound for Sequential Sensing of Picric Acid and Aliphatic Amines: Physicochemical Details and Construction of Molecular Logic Gates

Ghosh

Seth

Ghosh

et al. 2021

Chemistry An Asian Journal

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Picric acid (PA) at low concentration is a serious water pollutant. Alongside, aliphatic amines (AAs) add to the queue to pollute surface water. Plenty of reports are available to sense PA with an ultralow limit of detection (LOD). However, only a handful of works are testified to detect AAs. A new fluorescent donor-acceptor compound has been synthesized with inherent intramolecular charge transfer (ICT) character that enables selective and sensitive colorimetric quantitative detection of PA and AAs with low LODs in nonaqueous as well as aqueous solutions. The synthesized compound is based on a hemicyanine skeleton containing two pyridenylmethylamino groups at the donor and a benzothiazole moiety at the acceptor ends. The detailed mechanisms and reaction dynamics are explained spectroscopically along with computational support. The fluorescence property of the detecting compound changes due to protonation of its pyridinyl centers by PA leading to quenching of fluorescence and subsequently de-protonation by AAs to revive the signal. We have further designed logic circuits from the acquired optical responses by sequential interactions.

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“…In this context, fluorescent probes have emerged as a rapid, simple, and accurate molecular tool to detect trace amounts of BAs. Optical detection of BAs is mainly based on: (i) the use of functional organic dyes such as phenanthridines [ 15 ], naphthalenes [ 16 ], benzothiazoles [ 17 ], porphyrinoids [ 18 , 19 ]; (ii) supramolecular hydrogels [ 20 ]; and (iii) boron complexes [ 21 , 22 ]. Recently revised by A. Gupta, the aggregation-induced emission (AIE) phenomenon by different materials presents itself as a method with high potential for the detection of amines by an increase or a quench of the fluorescence process [ 23 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Catechol Derived Rosamine Dyes and Their Reactivity toward Biogenic Amines

et al. 2021

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Functional organic dyes play a key role in many fields, namely in biotechnology and medical diagnosis. Herein, we report two novel 2,3- and 3,4-dihydroxyphenyl substituted rosamines (3 and 4, respectively) that were successfully synthesized through a microwave-assisted protocol. The best reaction yields were obtained for rosamine 4, which also showed the most interesting photophysical properties, specially toward biogenic amines (BAs). Several amines including n- and t-butylamine, cadaverine, and putrescine cause spectral changes of 4, in UV–Vis and fluorescence spectra, which are indicative of their potential application as an effective tool to detect amines in acetonitrile solutions. In the gas phase, the probe response is more expressive for spermine and putrescine. Additionally, we found that methanolic solutions of rosamine 4 and n-butylamine undergo a pink to yellow color change over time, which has been attributed to the formation of a new compound. The latter was isolated and identified as 5 (9−aminopyronin), whose solutions exhibit a remarkable increase in fluorescence intensity together with a shift toward more energetic wavelengths. Other 9-aminopyronins 6a, 6b, 7a, and 7b were obtained from methanolic solutions of 4 with putrescine and cadaverine, demonstrating the potential of this new xanthene entity to react with primary amines.

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Multi-state amine sensing by electron transfers in a BODIPY probe

Abstract: Photoinduced electron transfer sets up the BODIPY probe for multi-state amine sensing by single-electron transfer then collisional quenching.

Cited by 20 publications

References 63 publications

Wireless Tags with Hybrid Nanomaterials for Volatile Amine Detection

Wireless Tags with Hybrid Nanomaterials for Volatile Amine Detection

A New Compound for Sequential Sensing of Picric Acid and Aliphatic Amines: Physicochemical Details and Construction of Molecular Logic Gates

Synthesis of Catechol Derived Rosamine Dyes and Their Reactivity toward Biogenic Amines

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