Tunable star-shaped triphenylamine fluorophores for fluorescence quenching detection and identification of nitro-aromatic explosives

Niamnont, Nakorn; Kimpitak, Nattaporn; Wongravee, Kanet; Rashatasakhon, Paitoon; Baldridge, Kim K.; Siegel, Jay S.; Sukwattanasinitt, Mongkol

doi:10.1039/c2cc34008a

Cited by 88 publications

(53 citation statements)

References 36 publications

(5 reference statements)

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“…As of now, fluorophores, conjugated polymers, and fluorescent quantum dots have been used as reporter materials. 3,4 In spite of the enormous attempts being made, the necessity of tagging makes it expensive to use these materials as sensors in real life applications. Also, appropriate exploration of fluorescent metal cluster-based sensors remains at a premature stage.…”

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confidence: 99%

Ultrafast on-site selective visual detection of TNT at sub-ppt level using fluorescent gold cluster incorporated single nanofiber

2015

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Ultrafast on-site selective visual detection of TNT at sub-ppt level using fluorescent gold cluster incorporated single nanofiber

2015

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“…3 Curved aromatic hydrocarbons related to corannulene have been used in various materials applications including the development of fluorescent chemosensors, 4 organic field-effect transistors, 5 and heterojunction photovoltaics. 6 In each case, specific photochemical and redox properties have been important to the success of the application.…”

Section: Introductionmentioning

confidence: 99%

Tunable Photochemical/Redox Properties of (Phenylthio)_ncorannulenes: Application to a Photovoltaic Device

Steinauer

Butterfield

Linden

et al. 2016

Journal of the Brazilian Chemical Society

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The additive substituent effect of phenylmercapto derivatives of corannulene are investigated by spectroscopic, electrochemical, and computational techniques. The per-substituted phenylmercaptocorannulene is incorporated as a replacement for [6,6]-phenyl-C 61 -butyric acid methyl ester (PCBM) in a photovoltaic device. Keywords: photovoltaic, electrochemistry, corannulene, photochemistry IntroductionIn a similar fashion to fullerenes, 1 curved aromatic hydrocarbons, like corannulene, 1, behave as electrondeficient π-systems, 2 the redox properties of which can be tuned by derivatization (Figure 1). 3 Curved aromatic hydrocarbons related to corannulene have been used in various materials applications including the development of fluorescent chemosensors, 4 organic field-effect transistors, 5 and heterojunction photovoltaics. 6 In each case, specific photochemical and redox properties have been important to the success of the application. Tuning the photochemical and redox properties of corannulene cognates corresponds to influencing the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) levels as well as the HOMO-LUMO gap. Whereas simple alkyl substituents raise HOMO and LUMO levels, 7 fluorinated alkyl groups lower both; 8 in neither case is there a substantial effect on the HOMO-LUMO gap as gauged from absorption spectroscopy. Organothio-substituents raise HOMO and lower LUMO levels such that one can obtain good electron acceptors with smaller HOMO-LUMO gaps. For example, compared to 1, a pale yellow material with first reduction at −2.33 eV in acetonitrile, decasubstitution of 1 with thiophenol (SPh) produces a deep red material with the first reduction potential at −1.22 eV, 10 which is similar to the reported value of −1.17 volts for [6,6]-phenyl-C 61 -butyric acid methyl ester (PCBM). Given that many high-performing organic photovoltaic (OPV) devices rely on C 60 and its derivatives to act as electron acceptors, 11 this similarity in electrochemistry between PCBM and decakisphenylmercaptocorannulene motivates a study into the nature of tuning the physical properties (electrochemistry, ultraviolet-visible (UV-Vis) absorption, fluorescence, and phosphorescence) of corannulene by phenylmercapto substitution and the photovoltaic characterization of decakis(phenylthio-)corannulene as an acceptor in an OPV device. Furthermore, the optoelectronic tunability of corannulenes makes them potentially useful as organic light emitting diodes (OLEDs), 12 as organic conductors, 13 or in high density carbon electrodes. Vol. 27, No. 10, 2016 ExperimentalGeneral synthesis 1,3-Dimethyl-2-imidazolidinone (DMI; 5-10 mL, dried over molecular sieve) was added to a round bottom flask equipped with a reflux condenser. Thiophenol (1.5 equiv./ reaction site) and sodium hydride (1.2 equiv./reaction site, 60% in mineral oil) were added and stirred at room temperature for 10 min. The halogenated corannulene derivative (2a-7a, 1 equiv.) was added and the solution was heated at 60 °C for 18 h. The...

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“…By repetition of a sequence based on a [3+2] cycloaddition and an acid–amine coupling reaction, compound 9 was afforded. The [3+2] cycloaddition between compound 9 and 1‐azopyrene15 gave compound L1 in 56 % yield, and subsequent reactions produced compounds L2 and L3 in 45 % and 43 % yields. The COSY and NOESY spectra were used to assign protons of the receptor L2 in detail (Figure S1 in the Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 1,2,3‐Triazole‐4‐carboxamide‐Containing Foldamers for Sulfate Recognition

et al. 2014

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A series of triazolecarboxamide‐containing foldamers were synthesized from simple starting materials by means of repeated [3+2] cycloadditions) and acid–amine coupling reactions. Foldamer–anion binding behavior and affinities were determined by 1H NMR titration in [D2]dichloromethane. The selective recognition of sulfate by these motifs was studied by one‐ and two‐dimensional (1H, 1H‐1H COSY and NOESY) NMR spectroscopy as well as UV/Visible and fluorescence titrations. The structures of the triazolecarboxamide‐containing foldamers can be optimized for highly selective recognition of sulfate anions by changing the numbers of triazolecarboxamide units and by the introduction of electron‐withdrawing substituents on the terminal benzene ring. These findings indicate the importance of the structural compatibility between the receptor and anions for the highly selective anion binding as well as the electronic effect on tuning the anion‐binding affinities of receptors.

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Tunable star-shaped triphenylamine fluorophores for fluorescence quenching detection and identification of nitro-aromatic explosives

Abstract: Triphenylamine-based fluorophores containing pyrene or corannulene show variable fluorescence quenching sensitivity toward nitro explosives. The most sensitive fluorophore is capable of detecting TNT on the ng cm(-2) scale; the array is useful for identifying nitro aromatics.

Cited by 88 publications

References 36 publications

Ultrafast on-site selective visual detection of TNT at sub-ppt level using fluorescent gold cluster incorporated single nanofiber

Ultrafast on-site selective visual detection of TNT at sub-ppt level using fluorescent gold cluster incorporated single nanofiber

Tunable Photochemical/Redox Properties of (Phenylthio)_ncorannulenes: Application to a Photovoltaic Device

Synthesis of 1,2,3‐Triazole‐4‐carboxamide‐Containing Foldamers for Sulfate Recognition

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Tunable star-shaped triphenylamine fluorophores for fluorescence quenching detection and identification of nitro-aromatic explosives

Abstract: Triphenylamine-based fluorophores containing pyrene or corannulene show variable fluorescence quenching sensitivity toward nitro explosives. The most sensitive fluorophore is capable of detecting TNT on the ng cm(-2) scale; the array is useful for identifying nitro aromatics.

Cited by 88 publications

References 36 publications

Ultrafast on-site selective visual detection of TNT at sub-ppt level using fluorescent gold cluster incorporated single nanofiber

Ultrafast on-site selective visual detection of TNT at sub-ppt level using fluorescent gold cluster incorporated single nanofiber

Tunable Photochemical/Redox Properties of (Phenylthio)ncorannulenes: Application to a Photovoltaic Device

Synthesis of 1,2,3‐Triazole‐4‐carboxamide‐Containing Foldamers for Sulfate Recognition

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Tunable Photochemical/Redox Properties of (Phenylthio)_ncorannulenes: Application to a Photovoltaic Device