Self-Assembled Pentacenequinone Derivative for Trace Detection of Picric Acid

Bhalla, Vandana; Gupta, Ankush; Rao, D. S. Shankar; Prasad, S. Krishna

doi:10.1021/am302132h

Cited by 195 publications

(139 citation statements)

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“…17 The functionalization of acenes is mainly focused on appending alkyl, aryl, and alkyne residues to the framework in order to tune the HOMO− LUMO gap and the arrangement in the solid state. 16a, 18 Recently, we have reported on the synthesis of carbon-rich ruthenium allenylidene complexes based on pentacenequinone, which provided molecules with interesting structural and electronic properties. 19 Thus, herein, we describe the extension of our efforts on the synthesis of new 18 VE [Ru(bdmpza)-Cl(PPh 3 ) 2 ] based allenylidene complexes derived from a series of polyaromatic propargyl alcohols.…”

Section: ■ Introductionmentioning

confidence: 99%

Carbon-Rich Ruthenium Allenylidene Complexes Bearing Heteroscorpionate Ligands

et al. 2014

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A series of ruthenium allenylidene complexes bearing polyaromatic substituents have been prepared starting from [Ru(bdmpza)Cl(PPh 3 ) 2 ] (1) (bdmpza = bis(3,5-dimethylpyrazol-1-yl)acetato). Reacting 1 with 1,1-bis(3,5-ditert-butylphenyl)-1-methoxy-2-propyne results in the formation of two structural isomers of an allenylidene complex [Ru(bdmpza)Cl(CCC(Ph t Bu 2 ) 2 )(PPh 3 )] (5A/5B), as well as the related carbonyl complex [Ru(bdmpza)Cl(CO)-(PPh 3 )] (4A/4B). Conversion of 9-ethynyl-9-fluorenol leads to the corresponding allenylidene complex [Ru(bdmpza)Cl(CC(FN))(PPh 3 )] (7A/7B) (FN = fluorenyl). Based on anthraquinone, a new synthetic route toward 10-ethynyl-10-hydroxyanthracen-9-one via the trimethylsilyl-protected propargyl alcohol is described, and subsequent conversion of this compound to the allenylidene complex ([Ru(bdmpza)Cl(C C(AO))(PPh 3 )] (12A/12B) (AO = anthrone) is reported. The synthetic route from 7H-benzo[no]tetraphen-7-one to the propargyl alcohol 7-ethynyl-7H-benzo[no]tetraphen-7-ol is described, which is followed by the transformation into the allenylidene complex [Ru(bdmpza)Cl(CC(BT))(PPh 3 )] (17A/17B) (BT = benzotetraphene). The molecular structures of 4B, 7A, 7B, 12A, 12B, 13A, and 17A have been characterized by single-crystal X-ray crystallography, and these analyses suggest that 17A might function as a "metal-tuned organic field effect transistor". The electrochemical properties of the allenylidene complexes have been studied via cyclic voltammetry, and time-dependent DFT calculations have been conducted to assign weak absorptions in the NIR region to forbidden MLCT transitions. ■ INTRODUCTIONOrganometallic complexes containing allenylidene moieties are of considerable interest due to their characteristic chemical and physical properties. 1 The synthesis of cumulene based complexes has benefited immensely from the methodology published by Selegue. 2 The reaction of substituted propargyl alcohols with a variety of ruthenium based metal complexes allows for the direct formation of ionic and neutral complexes, and this has dramatically simplified the synthetic demand for such work. π-Conjugated systems based on ruthenium are important in systems that allow exchange of electrons via the cumulenylidene unit between remote terminal groups, 3 thus leading to interesting properties and potential applications in molecular-scale electronic, magnetic, and optical devices. 4 Special attention has been put on dinuclear compounds that can communicate along the allenylidene unit. The linking between the two metal centers can be achieved either via functionalization of the allenylidene with nitrogen based donor substituents, as in the bis(pyridyl)allenylidene−ruthenium(II) complex trans-[Cl(16-TMC)RuCCC(2-py) 2 ] + 5,9,5,9, py = pyridyl), 5 or via all carbon linked systems such as trans-[Cl(dppe) 2 Ru−CC−C(CH 3 )C(H)−C(CH 3 )CC Ru(dppe) 2 Cl]BF 4 , which results from the coupling of the diynyl and allenylidene moieties. 6 Nevertheless, classical mononuclear ruthenium allenylide...

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Section: ■ Introductionmentioning

confidence: 99%

Carbon-Rich Ruthenium Allenylidene Complexes Bearing Heteroscorpionate Ligands

et al. 2014

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“…In this work, we report a new three-dimensional (3D) metalorganic framework sensor with the molecular formula (C 2 H 6 -NH 2 ) 2 [Tb 2 (ptptc) 2 and terbium nitrate under solvothermal conditions and characterized by XRD, elemental analysis, IR spectra, TG analysis. This 3D framework containing one-dimensional (1D) channels along a and b axis, which are expected to facile the diffusion and concentration of analytes and the host-guest interactions.…”

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confidence: 99%

A novel microporous Tb-MOF fluorescent sensor for highly selective and sensitive detection of picric acid

Zhang

Jiang

et al. 2018

RSC Adv.

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A new three-dimensional metal-organic framework (MOF) sensor with molecular formula (C 2 H 6 NH 2 ) 2 [Tb 2 (ptptc) 2 (DMF)(H 2 O)]$DMF$6H 2 O (complex 1) has been constructed from terphenyl-3,3 0 ,5,5 0 -tetracarboxylic acid (H 4 ptptc) and terbium nitrate under solvothermal conditions. The structure of complex 1 was characterized by single-crystal X-ray diffraction analysis (XRD), elemental analysis, IR spectroscopy and thermogravimetric (TG) analysis, and the purity was further confirmed by powder X-ray diffraction (PXRD) analysis. XRD analysis reveals that complex 1 crystallizes in a triclinic system P 1 space group and consists of a three-dimensional anionic network which has one-dimensional channels. Fluorescence titration experiments showed that complex 1 displayed real-time, highly selective and sensitive fluorescence quenching behavior towards picric acid with a nanomolar scale experimental detection limit (100 nM). Recycling titration experiments suggested that the as-synthesized probe has good reversibility and can be used for at least five cycles in fluorescence titration experiments without obvious fluorescence intensity reduction or framework structure destruction. Furthermore, the high selectivity and sensitivity as well as good recyclability of complex 1 make it a potential fluorescent sensor for picric acid.

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“…13,14 Therefore, selective and sensitive detection of TNP has attracted increasing attention in view of homeland security and personal safety.…”

Section: -12mentioning

confidence: 99%

A long-persistent phosphorescent chemosensor for the detection of TNP based on CaTiO₃:Pr³⁺@SiO₂ photoluminescence materials

Wang

et al. 2018

RSC Adv.

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Self-Assembled Pentacenequinone Derivative for Trace Detection of Picric Acid

Cited by 195 publications

References 77 publications

Carbon-Rich Ruthenium Allenylidene Complexes Bearing Heteroscorpionate Ligands

Carbon-Rich Ruthenium Allenylidene Complexes Bearing Heteroscorpionate Ligands

A novel microporous Tb-MOF fluorescent sensor for highly selective and sensitive detection of picric acid

A long-persistent phosphorescent chemosensor for the detection of TNP based on CaTiO₃:Pr³⁺@SiO₂ photoluminescence materials

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Self-Assembled Pentacenequinone Derivative for Trace Detection of Picric Acid

Cited by 195 publications

References 77 publications

Carbon-Rich Ruthenium Allenylidene Complexes Bearing Heteroscorpionate Ligands

Carbon-Rich Ruthenium Allenylidene Complexes Bearing Heteroscorpionate Ligands

A novel microporous Tb-MOF fluorescent sensor for highly selective and sensitive detection of picric acid

A long-persistent phosphorescent chemosensor for the detection of TNP based on CaTiO3:Pr3+@SiO2 photoluminescence materials

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A long-persistent phosphorescent chemosensor for the detection of TNP based on CaTiO₃:Pr³⁺@SiO₂ photoluminescence materials