9-Dicyanomethylene-2,4,7-trinitrofluorene, A New Electron Acceptor

Mukherjee, Tapan Kumar; Levasseur, Leonard A.

doi:10.1021/jo01013a504

Cited by 59 publications

(17 citation statements)

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“…(2,4,7-Trinitro-9H-fluoren-9-ylidene)propanedinitrile (2) was prepared from 2,4,7-trinitro-9-fluorenone and malononitrile according to Mukherjee [39].…”

Section: Discussionmentioning

confidence: 99%

Reaction of 4‐substituted thiosemicarbazides with (2,4,7‐trinitro‐9H‐fluoren‐9‐ylidene)propanedinitrile

Hassan

Ibrahim

Shawky

et al. 2006

Journal of Heterocyclic Chem

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4-Substituted thiosemicarbazides 4a-c reacted with (2,4,7-trinitro-9H-fluoren-9-ylidene)-propanedinitrile (2) in pyridine with admission of air to form spiro[fluorene-9,3'-(1,2,4-triazole)]derivatives 5a-c and (4-substituted thiosemicarbazono)propanedinitriles 6a-c in modest yields. 2,4,7-Trinitro-9-fluorenone (8) as well as one reduction product thereof and of 2, namely compounds 9 and 10, respectively are also found. A rationale for the conversions observed is presented.

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“…(2,4,7-Trinitro-9H-fluoren-9-ylidene)propanedinitrile (2) was prepared from 2,4,7-trinitro-9-fluorenone and malononitrile according to Mukherjee [39].…”

Section: Discussionmentioning

confidence: 99%

Reaction of 4‐substituted thiosemicarbazides with (2,4,7‐trinitro‐9H‐fluoren‐9‐ylidene)propanedinitrile

Hassan

Ibrahim

Shawky

et al. 2006

Journal of Heterocyclic Chem

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“…The derivated molecules of 9-fluorenone (I, II and III) were synthesized by direct nitration [2] and the other three acceptor molecules (IV, V and VI) by the Mukherjee's method [3]. The charge transfer complexes were prepared by warm equimolar diluted solution of commercially available TTF and the respective fluorene derivative in acetonitrile.…”

Section: Sample Preparationmentioning

confidence: 99%

Infrared And Raman Spectroscopy Of Organic Electron Conductors

Ridaura¹,

Gómez²,

Marquina³

et al. 1993

MRS Proc.

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FT-Raman and infrared (IR) spectra of a series of TTF-fluorene derivative family were obtained using a conventional IR spectrometer and a FT-Raman spectrometer. The Raman shifts of the observed band (v 3 stretching band) changes from sample to sample and we correlate these changes with the degree of charge transfer between the donor (TTF) and the acceptor (fluorene derivative) molecules. These results are compared with those obtained from changes in the IR absorption frequencies of the C-N stretching mode in the acceptor molecule.

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“…Eastman Kodak White Label DC I BQ was crystallized twicc from 30-60°C petroleum ether and sublimed undcr vacuum. DCMTNF, prepared following Mukherjee (36) and purified by recrystallizing twice from AN, had mp 263-264°C (lit. (36) mp 266-268°C).…”

Section: Reagerzrs and Solverirsmentioning

confidence: 99%

“…(36) mp 266-268°C). DCMTENF (37) was prepared from 2,4.5,7-tctranitrofluorenone and malononitrile following thc procedure used to prepare DCMTNF (36) and purified by recrystallizing twice from AN, mp ca. 380-382°C (dec.) (lit.…”

Section: Reagerzrs and Solverirsmentioning

confidence: 99%

“…In reaction of DD with six of the oxidants the formation of D' was followed at 357 nm (BQ, CA, TCNE, DCBQ, co(bipy);') or at 420 nm (DCIBQ, CA, DCBQ, co(bipy);'). The formation of the acceptor radical anion was followed for DCMTNF (440, 550, or 600 nm) (36,43), DCNQ (520 nm) ( a ) , DCMTENF (550 nm) ( 4 3 , TCNQ (680 nrn) (46) and DCNNQ (520 nm) (47). Oxidation of 2,2'-and 3,3'-dimethoxy-DD by CA and co(bipy):') was followed at the 2-and 3-methoxy-D' absorption at 367 nm.…”

Section: Kinetic Measurementsmentioning

confidence: 99%

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Kinetics and mechanism of oxidation of N,N′-dimethyl-9,9′-biacridanyl by some π acceptors and a one-electron oxidant

Colter¹,

Lai²,

Parsons³

et al. 1985

Can. J. Chem.

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Oxidation of N,N′-dimethyl-9,9′-biacridanyl (DD) has been investigated as a model for single electron transfer (SET)-initiated oxidation of NADH coenzyme models such as N-methylacridan (DH). Oxidants investigated cover a 1010-fold range of reactivity in acetonitrile and include the π acceptors 1,4-benzoquinone (BQ), 2,6-dichloro-1,4-benzoquinone (DCIBQ), p-chloranil (CA), 2,3-dicyanobenzoquinone (DCBQ), 2,3-dicyano-1,4-naphthoquinone (DCNQ), 2,3-dicyano-5-nitro-1,4-naphthoquinone (DCNNQ), 9-dicyanomethylene-2,4,7-trinitrofluorene (DCMTNF), 9-dicyanomethylene-2,4,5,7-tetranitrofluorene (DCMTENF), 7,7,8,8-tetracyanoquinodimethane (TCNQ), and tetracyanoethylene (TCNE), and the one-electron oxidant tris(2,2′-bipyridyl)cobalt(III), [Formula: see text] The oxidation product is, in every case, N-methylacridinium ion (D+). A mechanism involving a rate-determining electron transfer with simultaneous fragmentation to D+ and N-methyl-9-acridanyl radical (D•) is proposed. This mechanism is supported by the observed dependence of the rate on oxidant reduction potential, by spin-trapping experiments, by kinetic isotope effects in oxidation of 9,9′-dideuterio-DD, and by substituent effects in oxidation of 2,2′- and 3,3′-dimethoxy-DD. The rate of oxidation of DD relative to that of DH is 3.4 × 102 with [Formula: see text] and with the π acceptors varies from ea. 0.3 (BQ) to 8.1 × 104 (DCMTENF). The results rule out a SET-initiated mechanism for oxidation of DH by all of the oxidants studied except TCNQ and DCMTENF.

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9-Dicyanomethylene-2,4,7-trinitrofluorene, A New Electron Acceptor

Cited by 59 publications

References 0 publications

Reaction of 4‐substituted thiosemicarbazides with (2,4,7‐trinitro‐9H‐fluoren‐9‐ylidene)propanedinitrile

Reaction of 4‐substituted thiosemicarbazides with (2,4,7‐trinitro‐9H‐fluoren‐9‐ylidene)propanedinitrile

Infrared And Raman Spectroscopy Of Organic Electron Conductors

Kinetics and mechanism of oxidation of N,N′-dimethyl-9,9′-biacridanyl by some π acceptors and a one-electron oxidant

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