A ‘chemically-gated’ photoresponsive compound as a visible detector for organophosphorus nerve agents

Nourmohammadian, Farahnaz; Wu, Tuoqi; Branda, Neil R.

doi:10.1039/c1cc13685b

Cited by 55 publications

(28 citation statements)

References 30 publications

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“…In addition, Branda and coworkers51 reported an analogue (compound 30 depicted in Figure ) whose photochromism was suppressed by the formation of the intramolecular hydrogen bonding between the phenol hydrogen and the carbonyl oxygen in cyclohexane. 30 worked equally well in solution and in an immobilized state when exposed to vapors of an organophosphate to generate colorless compound 31 , which underwent ring‐closing when exposed to UV light and produced an easily observable change in color.…”

Section: Photochromic Molecular Switchesmentioning

confidence: 99%

Photochromic Materials: More Than Meets The Eye

2012

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Photochromic materials are a family of compounds which can undergo reversible photo-switches between two different states or isomers with remarkably different properties. Inspired by their smart photo-switchable characteristics, a variety of light-driven functional materials have been exploited, such as ultrahigh-density optical data storage, molecular switches, logic gates, molecular wires, optic/electronic devices, sensors, bio-imaging and so on. This review commences with a brief description of exciting progress in this field, from systems in solution to modified functional surfaces. Further development of these photo-switchable systems into practical applications as well as existing challenges are also discussed and put in prospect.

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Section: Photochromic Molecular Switchesmentioning

confidence: 99%

Photochromic Materials: More Than Meets The Eye

2012

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“…[22][23][24][25][26][27] Scarcely investigated, association of the two photochemical processes, ESIPT and 6p electrocyclization of diarylethenes, within the same molecule has yet led to appealing features such as chemically gated photochromism in few dithienylmaleimide derivatives [28] and also the design of a dithienylmaleimide-based probe for a naked-eye detection of volatile neurotoxic organophosphates. [29] A better understanding of the interplay between the two important photochemical processes is of great interest not only from an academic viewpoint, but also for designing novel photoswitchable systems. 1 a is an excellent candidate for such studies because two ESIPT processes are possible, between the hydrogen atom of each phenolic hydroxy group and the nitrogen atom of the neighboring thiazolyl group, and the two potential ESIPT sites are closely conjugated with the 6p electrocyclization backbone, which would favor strong interactions between the two photochemical processes.…”

Section: Introductionmentioning

confidence: 99%

A Multifunctional Photoswitch: 6π Electrocyclization versus ESIPT and Metalation

Guérin

Léaustic

Delbaere

et al. 2014

Chemistry A European J

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A terthiazole-based molecular switch associating 6π electrocyclization, excited state intramolecular proton transfer (ESIPT), and strong metal binding capability was prepared. The photochemical and photophysical properties of this molecule and of the corresponding nickel and copper complexes were thoroughly investigated by steady-state and ultrafast absorption spectroscopy and rationalized by DFT/TDDFT calculations. The switch behaves as a biphotochrome with time-dependent photochemical outcome and displays efficient ESIPT-based fluorescence photoswitching. Both photochemical reactions are suppressed by nickel or copper metalation, and the main factors contributing to the quenching of the electrocyclization are discussed.

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“…Electron-rich extended conjugated molecules are promising organic candidates for electronic materials [1] such as field effect transistors [2], solar cells [3], light emitting diodes [4], detectors [5], and sensors [6]. The efficiency of the charge transport is the key to obtain high-performance electronic materials.…”

Section: Introductionmentioning

confidence: 99%

Computational studies of π–π interactions in dimers of heterosubstituted sumanenes

Karunarathna

Sæbø

2015

Struct Chem

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A computational study of dimers of heterosubstituted sumanenes has been carried out using a dispersion-corrected density functional theory method. In the heterosubstituted systems, the three bridging CH 2 groups of sumanene have been replaced by O, NH, and S. For each dimer system, two motifs, staggered and eclipsed forms, were considered. The most stable geometry was the staggered stacked concave-convex motif where one monomer was rotated by 60°from the eclipsed configuration. The calculated binding energies and equilibrium distances of the staggered concave-convex dimers are predicted to be 20.1 kcal/mol and 3.7 Å for the parent sumanene molecule, 17.4 kcal/mol and 3.8 Å , 12.3 kcal/mol and 3.7 Å , and 16.6 kcal/mol and 3.7 Å for the NH-, O-, and S-substituted analogs, respectively. The binding energies of the dimers have been analyzed in terms of dipole-dipole contributions, dispersion contributions, and C-HÁÁÁp interactions.

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A ‘chemically-gated’ photoresponsive compound as a visible detector for organophosphorus nerve agents

Abstract: We describe a versatile and convenient visible detection method for organophosphorus compounds based on a colorless 'pro-photoresponsive' organic molecule that undergoes photochemical ring-closing to produce a colored isomer only after it reacts with vapors of the phosphorylating agent.

Cited by 55 publications

References 30 publications

Photochromic Materials: More Than Meets The Eye

Photochromic Materials: More Than Meets The Eye

A Multifunctional Photoswitch: 6π Electrocyclization versus ESIPT and Metalation

Computational studies of π–π interactions in dimers of heterosubstituted sumanenes

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