Directly-linked intramolecular donor–acceptor compounds of ferrocene and tetracyanoanthraquinodimethane

Kelly, Glenn; Darviche, Fatémeh; Robertson, Neil; Gelbrich, Thomas; Hursthouse, Michael B.; Thomas, Dafydd A.; Butler, Ian R.

doi:10.1016/j.inoche.2005.06.011

Cited by 9 publications

(7 citation statements)

References 31 publications

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“…Anthocyanins are radicals of different natures, one donor and one acceptor and have a large third-order nonlinearity since the radicals add their effects, thus intensify the asymmetric distortion of the conjugated system. Further the electronic properties of this type of molecule exhibit a unusual property, the intramolecular (Kelly et al 2005) charge transfer between the two radicals.…”

Section: Resultsmentioning

confidence: 99%

Computations of absorption spectra and nonlinear optical properties of molecules based on anthocyanidin structure

et al. 2014

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Simulation of UV-VIS spectra and microscopic third-order nonlinear optical (NLO) coefficients at 532 nm wavelength of molecules based of anthocyanidin structure in gas phase environment using semi-empirical PM3 method was calculated. One-photon absorption characterizations of the investigated molecules have been theoretically obtained by configuration interaction method with doubly occupied molecular orbitals. Estimated theoretical spectra shows a sensibility to the different functional groups such as hydroxyl and methoxyl substitution in radicals. These groups causes red shift in absorption spectra in comparison to the other samples what agree well with the experimental data. Adjunction of such functional donor character group in the investigated molecule slightly decreases the HOMO-LUMO energy splitting gap but increases the ground state dipole moment resulting the substantial increase of NLO coefficient in this system comparing to the other samples.According to presented investigations the tested molecules have large nonlinear optical properties.

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Section: Resultsmentioning

confidence: 99%

Computations of absorption spectra and nonlinear optical properties of molecules based on anthocyanidin structure

et al. 2014

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“…This kind of molecules has third-order nonlinearity with non-zero hyperpolarizabilities since the radicals increase their NLO effects, and thus intensify the asymmetric distortion of the conjugated system. Furthermore, the electronic properties of these molecules exhibit an unusual property, characterizing the intramolecular charge transfer between the two radicals [20]. We have found rather similar average dipole polarizabilities for all the investigated compounds (see Tables 2-3).…”

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confidence: 53%

Ab-initio calculations on static and dynamic third-order optical nonlinearity of azo-azulenes

Sahraoui¹,

Karakas²,

Kouari³

et al. 2012

Photon. Lett. Poland

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“…Ferrocenylanthracenes have been prepared either by reaction of diazonium derivatives of anthraquinone with ferrocene, and subsequent reduction to the corresponding anthracenes, or more directly by palladium‐catalyzed coupling procedures , , . In the present case, 1,1′‐di(9‐anthracenyl)ferrocene, 1 , was prepared by the palladium‐catalyzed coupling of ferrocene‐1,1′‐di‐boronic acid ester with 9‐bromoanthracene.…”

Section: Resultsmentioning

confidence: 99%

Syntheses, Structures and Dynamics of 9‐(Ferrocenylmethyl)anthracene and Related Molecular Gears: Phosphorus to the Rescue!

et al. 2018

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The rotational barriers of the anthracenyl and triptycyl units in 1‐(9‐anthracenyl)‐1′‐(9‐triptycyl)ferrocene were independently measured as 11.6 and 17.6 kcal mol–1, respectively. Attempts to reduce 9‐ferrocenoylanthracene to 9‐(ferrocenylmethyl)anthracene, 3, in which the sandwich moiety and the planar aromatic are linked through an angular methylene unit, were thwarted by reduction of the anthracene moiety to form 9‐ferrocenylmethyl‐9,10‐dihydroanthracene, 5, and 9‐ferrocenoyl‐9,10‐dihydroanthracene, 6. However, treatment of phenyl(ferrocenyl)methanol, 9, with triphenylphosphine and triflic acid gave [(phenyl)(ferrocenyl)methyl]phosphonium triflate, 10; subsequent hydrolysis yielded benzylferrocene (93 %). Analogously, (9‐anthracenyl)(ferrocenyl)methanol, 11, and Ph3P/TfOH furnished 3 (up to 92 %) together with various amounts of its anthracenylidene tautomer, 15, depending on the hydrolysis conditions. Surprisingly, during the chromatographic purification of 11, partial dehydration occurred to give di[(9‐anthracenyl)(ferrocenyl)methyl] ether, 12. The fluxional dynamics of 3, 11 and 12 are very different: anthracenyl rotation of the group in 3 and 11 is facile (barriers of < 9 and ≈ 9.6 kcal mol–1, respectively), but is arrested in 12 due to mutual steric locking of the two anthracenes. Diels–Alder addition of benzyne to 3 furnished 9‐(ferrocenylmethyl)triptycene, 16. The molecular structures of 3, 5, 9, 10, 11, 12 and 16 were determined by X‐ray crystallography.

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Directly-linked intramolecular donor–acceptor compounds of ferrocene and tetracyanoanthraquinodimethane

Cited by 9 publications

References 31 publications

Computations of absorption spectra and nonlinear optical properties of molecules based on anthocyanidin structure

Computations of absorption spectra and nonlinear optical properties of molecules based on anthocyanidin structure

Ab-initio calculations on static and dynamic third-order optical nonlinearity of azo-azulenes

Syntheses, Structures and Dynamics of 9‐(Ferrocenylmethyl)anthracene and Related Molecular Gears: Phosphorus to the Rescue!

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