Cyanide Detection Using a Triazolopyridinium Salt

Robbins, Thomas F.; Qian, Hai; Su, Xin; Hughes, Russell P.; Aprahamian, Ivan

doi:10.1021/ol4008298

Cited by 77 publications

(24 citation statements)

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“…Recently, we reported on a new family of [1,2,3]triazolo[1,5‐a]pyridinium salts that i) can be easily prepared from the corresponding hydrazones, ii) exhibit good solubility in water, and iii) have promising photophysical properties, including blue‐light emission . In this article we report on the extended family of these water‐soluble triazolopyridinium species ( 1 a – e ) in addition to the triazoloquinolinium species 2 a , b that have an expanded π‐system.…”

Section: Introductionmentioning

confidence: 99%

“…[12] Ag eneral drawback of most current approaches, however,i st hat the efficiency of blue-light emitters is usually reduced upon going from solution (wheret hey are usually characterizeda nd studied) to the solid-state by intermolecular interactions that lead to severes elf-quenching and bathochromic shifts. [13] Recently,w er eported on an ew familyo f[ 1,2,3]triazolo[1,5a]pyridinium salts [14] that i) can be easily preparedfrom the corresponding hydrazones, [15][16][17] ii)exhibit good solubility in water, and iii)have promising photophysical properties, including blue-light emission. [14] In this article we report on the extended family of these water-soluble triazolopyridinium species (1a-e) in addition to the triazoloquinolinium species 2a,b that have an expanded p-system.…”

Section: Introductionmentioning

confidence: 99%

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Blue‐Light‐Emitting Triazolopyridinium and Triazoloquinolinium Salts

Carboni

Qian

et al. 2017

ChemPhotoChem

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Compounds that emit blue light are of interest for applications that include optoelectronic devices and chemo/biosensing and imaging. The design and synthesis of small organic molecules that can act as high‐efficiency deep‐blue‐light emitters in the solid state and can be easily processed from solutions represents a significant challenge. Herein we present the preparation and photophysical, photochemical and electrochemical properties of a series of triazolopyridinium and triazoloquinolinium compounds. The compounds are soluble in water or polar organic solvents and exhibit photoluminescence in the blue region of the spectrum in fluid solution, in the solid state and in a frozen matrix.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Blue‐Light‐Emitting Triazolopyridinium and Triazoloquinolinium Salts

Carboni

Qian

et al. 2017

ChemPhotoChem

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“…In this connection, a good number of literature reports are there on colorimetric probes for cyanide ion but the fluorimetric as well as colorimetric probes for cyanide are very less common . Out of numerous adopted strategies viz cyanide affinity to metal complexes, hydrogen bonding, nucleophilic addition, chemical reaction based molecular fluorescent probes attract attention because of their high selectivity and sensitivity . However, the synthesis of fluorescent chemosensors and predicting the mechanism behind sensing has remained a focus for most of the studies, but detailed mechanisms of sensing are still lacking.…”

Section: Introductionmentioning

confidence: 99%

Intramolecular Charge Transfer: Mechanism Behind Cyanide Anion Sensing of 3,5‐Diformyl–borondipyrromethene

Bhat

Jha

2017

ChemistrySelect

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The synthesis of fluorescent chemosensors has remained a focus for most of the studies, but detailed mechanisms of sensing are still lacking. Density functional theory (DFT) and time dependent-density functional theory (TD-DFT) methods have been utilized to investigate the cyanide anion sensing mechanism of 3,5-diformyl-borondipyrromethene (1). The natural charges on carbons of the formyl groups of 1 indicate that these carbons are prone to nucleophilic addition. The analysis of the frontier molecular orbitals designates the first excited state (S 1 ) of 1 as a local excited state with p ! s* transition. Likewise, S 1 of 2 (the cyano form of 1) is a charge separated state, showing intramolecular charge transfer (ICT) which is responsible for inducing the fluorescence quenching in 2.[a] Dr.

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“…Hydrazones, structurally related to imines, are a class of compounds containing the CNN group, and also widely used in molecular switches, and other fields of chemistry . Recently, the effect of substitution type and position on the photochromic properties of acylhydrazones, characterized by the CNN and CO motifs, have been exploited experimentally by Hecht and coworkers .…”

Section: Introductionmentioning

confidence: 99%

A theoretical study of the excited-state decay of acylhydrazones

Cao

2016

Int. J. Quantum Chem.

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Acylhydrazones is a novel yet underexploited class of molecular switches. In the present paper, we investigated the excited-state decay of three model systems of acylhydrazones in the gas phase by a combination of electronic structure calculations and Tully's surface hopping dynamic simulations. Our computational results demonstrated that the S 2 (n N p*) state decay of the three model systems leads to both the imine-like photo-isomerization through the S 1 (n N p*)/S 0 intersection and population of the S 1 (n O p*) state that will cross to the triplet manifold. The position of phenyl substituent was found to have an effect on the ratio of the two S 1 states. The present theoretical work provides some understandings of the intramolecular mechanism for de-population of the excited electronic states of acylhydrazones.acylhydrazones, internal conversion, intersystem crossing, molecular switches, photo-isomerization | I N T R O D U C T I O NMolecules that are able to undergo structural changes in response to light stimuli have attracted a great deal of interest because this type of molecules can be applied in a variety of functionalized materials. [1] The common photo-switchable molecules include azobenzenes, [2,3] diarylethene derivatives, [4,5] fulgides, [6] spiropyran and spirooxazine derivatives, [7,8] stilbenes, [9,10] catenanes and rotaxanes, [11,12] and molecular machines. [13][14][15] Hydrazones, structurally related to imines, are a class of compounds containing the C@NAN group, and also widely used in molecular switches, [16][17][18][19][20][21][22][23][24][25][26][27][28][29] and other fields of chemistry. [30][31][32][33][34][35][36][37][38][39][40] Recently, the effect of substitution type and position on the photochromic properties of acylhydrazones, characterized by the C@NAN and AC@O motifs, have been exploited experimentally by Hecht and coworkers. [41] They showed that acylhydrazones own advantages of remarkably facile preparation, highly fatigue resistance, and a higher degree of control over their properties. Also, under UV-irradiation, acylhydrazones were shown to exhibit good quantum yields (0.3-0.4 for E ! Z), which is between azobenzenes and diarylethenes in terms of efficiency. [42] Compared with hydrazones, acylhydrazone-based photoswitches pres-Int.

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Cyanide Detection Using a Triazolopyridinium Salt

Cited by 77 publications

References 65 publications

Blue‐Light‐Emitting Triazolopyridinium and Triazoloquinolinium Salts

Blue‐Light‐Emitting Triazolopyridinium and Triazoloquinolinium Salts

Intramolecular Charge Transfer: Mechanism Behind Cyanide Anion Sensing of 3,5‐Diformyl–borondipyrromethene

A theoretical study of the excited-state decay of acylhydrazones

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