Photochemistry of the pi-extended 9,10-bis(1,3-dithiol-2- ylidene)-9,10-dihydroanthracene system: Generation and characterisation of the radical cation, dication, and derived products

Jones, A.E.; Christensen, C.A.; Perepichka, D.F.; Batsanov, A.S.; Beeby, A.; Low, P.J.; Bryce, M.R.; Parker, A.W.

doi:10.1002/1521-3765(20010302)7:5<973::aid-chem973>3.0.co;2-#

Cavity ring-down spectroscopy of the torsional motions of 1,4-bis(phenylethynyl)benzene (2006)
Journal Article
Greaves, S., Flynn, E., Futcher, E., Wrede, E., Lydon, D., Low, P., …Beeby, A. (2006). Cavity ring-down spectroscopy of the torsional motions of 1,4-bis(phenylethynyl)benzene. The Journal of Physical Chemistry A, 110(6), 2114-2121. https://doi.org/10.1021/jp054426h

The torsional motions of jet-cooled 1,4-bis(phenylethynyl)benzene (BPEB), a prototype molecular wire, were studied using cavity ring-down spectroscopy in the first UV absorption band (316-321 nm). The torsional spectrum of 1,4-bis(phenylethynyl)-2,3,... Read More about Cavity ring-down spectroscopy of the torsional motions of 1,4-bis(phenylethynyl)benzene.

4,4 '-Diamino-2,2 ',6,6 '-tetramethylbiphenyl (2006)
Journal Article
Batsanov, A., Low, P., & Paterson, M. (2006). 4,4 '-Diamino-2,2 ',6,6 '-tetramethylbiphenyl. Acta crystallographica. Section E, E62, o2973-o2975. https://doi.org/10.1107/s1600536806022756

Each of the three independent molecules of the title compound, C16H20N2, has near-perpendicular benzene rings and pyramidal N atoms. Hydrogen bonding in the structure is rather inefficient.

The synthesis, structure, and electrochemical properties of Fe(C≡CC≡N)(dppe)Cp and related compounds. (2006)
Journal Article
Smith, M., Cordiner, R., Albesa-Jove, D., Yufit, D., Hartl, F., Howard, J., & Low, P. (2006). The synthesis, structure, and electrochemical properties of Fe(C≡CC≡N)(dppe)Cp and related compounds. Canadian Journal of Chemistry, 84(2), 154-163. https://doi.org/10.1139/v05-238

The cyanoacetylide complex Fe(C≡CC≡N)(dppe)Cp (3) is readily obtained from sequential reaction of Fe(C≡CSiMe3)(dppe)Cp with methyllithium and phenyl cyanate. Complex 3 is a good metalloligand, and coordination to the metal fragments [RhCl(CO)2], [Ru(... Read More about The synthesis, structure, and electrochemical properties of Fe(C≡CC≡N)(dppe)Cp and related compounds..

Improved syntheses of bis(ethynyl)-para-carboranes, 1,12-(RC C)(2)-1,12-C2B10H10 and 1,10-(RC equivalent to C)(2)-1,10-C2B8H8 (R = H or Me3Si). (2006)
Journal Article
Fox, M., Baines, T., Albesa-Jove, D., Howard, J., & Low, P. (2006). Improved syntheses of bis(ethynyl)-para-carboranes, 1,12-(RC C)(2)-1,12-C2B10H10 and 1,10-(RC equivalent to C)(2)-1,10-C2B8H8 (R = H or Me3Si). Journal of Organometallic Chemistry, 691(18), 3889-3894. https://doi.org/10.1016/j.jorganchem.2006.05.044

Copper-mediated cross-coupling reactions of the 12-vertex and 10-vertex para carboranes, 1,12-C2B10H12 and 1,10-C2B8H10, with trans-1-iodo-2-chloroethene gave the bis(trans-2-chloroethenyl) carboranes, 1,12-(ClCHdouble bond; length as m-dashCH)2-1,12... Read More about Improved syntheses of bis(ethynyl)-para-carboranes, 1,12-(RC C)(2)-1,12-C2B10H10 and 1,10-(RC equivalent to C)(2)-1,10-C2B8H8 (R = H or Me3Si)..

Trimetallic complexes featuring Group 10 tetracyanometallate dianions as bridging ligands. (2006)
Journal Article
Cordiner, R., Feroze, M., Lledo-Fernandez, C., Albesa-Jove, D., Howard, J., & Low, P. (2006). Trimetallic complexes featuring Group 10 tetracyanometallate dianions as bridging ligands. Inorganica Chimica Acta, 359(11), 3459-3466. https://doi.org/10.1016/j.ica.2005.10.001

The trimetallic complexes {Ru(PPh3)2Cp}2{μ-M(CN)4} and {Ru(dppe)Cp*}2{μ-M(CN)4} (M = Ni, Pd, Pt) have been prepared from reactions of RuCl(PPh3)2Cp or RuCl(dppe)Cp* with the appropriate tetracyanometallate salt, and structurally characterised. While... Read More about Trimetallic complexes featuring Group 10 tetracyanometallate dianions as bridging ligands..

Synthesis of new mer,trans-rhodium(III) hydrido-bis(acetylide) complexes: Structure of mer,trans- (PMe3)(3)Rh(C equivalent to C-C6H4-4-NMe2)(2)H (2006)
Journal Article
Zhu, X., Ward, R., Albesa-Jove, D., Howard, J., Porres, L., Beeby, A., …Marder, T. (2006). Synthesis of new mer,trans-rhodium(III) hydrido-bis(acetylide) complexes: Structure of mer,trans- (PMe3)(3)Rh(C equivalent to C-C6H4-4-NMe2)(2)H. Inorganica Chimica Acta, 359(9), 2859-2863. https://doi.org/10.1016/j.ica.2005.11.030

Terminal alkynes (R–Ctriple bond; length of mdashC–H, R = 1-naphthyl, 9-anthryl, 4-Me2N–C6H4–, or the longer analogue, 4-(4-Me2N–C6H4–Ctriple bond; length of mdashC–)–C6H4–) react with [Rh(PMe3)4Me] at ambient temperature, with loss of methane and on... Read More about Synthesis of new mer,trans-rhodium(III) hydrido-bis(acetylide) complexes: Structure of mer,trans- (PMe3)(3)Rh(C equivalent to C-C6H4-4-NMe2)(2)H.

Synthetic and structural studies on C-ethynyl- and C-bromo-carboranes. (2006)
Journal Article
Fox, M., Cameron, A., Low, P., Paterson, M., Batsanov, A., Goeta, A., …Schirlin, J. (2006). Synthetic and structural studies on C-ethynyl- and C-bromo-carboranes. Dalton Transactions, 29, 3544-3560. https://doi.org/10.1039/b517538k

A high-yield preparation of the C-monoethynyl para-carborane, 1-Me3SiC[triple bond, length as m-dash]C-1,12-C2B10H11, from C-monocopper para-carborane and 1-bromo-2-(trimethylsilyl)ethyne, BrC[triple bond, length as m-dash]CSiMe3 is reported. The low... Read More about Synthetic and structural studies on C-ethynyl- and C-bromo-carboranes..

Metal cluster terminated "molecular wires" (2006)
Journal Article
Khairul, W., Porres, L., Albesa-Jove, D., Senn, M., Jones, M., Lydon, D., …Low, P. (2006). Metal cluster terminated "molecular wires". Journal of Cluster Science, 17(1), 65-85. https://doi.org/10.1007/s10876-005-0041-x

The gold complexes Au(C≡CC6H4C≡CC6H4Me)(PPh3) (3) and {Au(PPh3)}2(μ-C≡CC6H4C≡CC6H4C≡CC6H4C≡C) (6), prepared from the reaction of AuCl(PPh3) with the corresponding terminal or trimethylsilyl protected alkynes, react readily with Ru3(CO)10(μ-dppm) to a... Read More about Metal cluster terminated "molecular wires".

Electronic interactions in bridged bis(cluster) assemblies - a comparison of para-CB10H10C, para-C6H4 and C-4 bridges (2005)
Journal Article
Le Guennic, B., Costuas, K., Halet, J., Nervi, C., Paterson, M., Fox, M., …Low, P. (2005). Electronic interactions in bridged bis(cluster) assemblies - a comparison of para-CB10H10C, para-C6H4 and C-4 bridges. Comptes rendus. Chimie, 8(11-12), 1883-1896. https://doi.org/10.1016/j.crci.2005.03.016

The electrochemical response of bis-Co2C2(CO)(4)(mu-dppm) complexes featuring bridging para-CB10H10C (5) and para-C6H4 (6) moieties are similar, each exhibiting two oxidations separated by ca. 100 mV, and two reductions separated by 80 mV, evidencing... Read More about Electronic interactions in bridged bis(cluster) assemblies - a comparison of para-CB10H10C, para-C6H4 and C-4 bridges.

The synthesis, structure, reactivity and electrochemical properties of ruthenium complexes featuring cyanoacetylide ligands (2005)
Journal Article
Cordiner, R. L., Smith, M. E., Batsanov, A. S., Albesa-Jové, D., Hartl, F., Howard, J. A., & Low, P. J. (2006). The synthesis, structure, reactivity and electrochemical properties of ruthenium complexes featuring cyanoacetylide ligands. Inorganica Chimica Acta, 359(3), 946-961. https://doi.org/10.1016/j.ica.2005.06.044

The complex [Ru(CCCN)(dppe)Cp*] (1) is readily obtained (ca. 70%) from the sequential reaction of [Ru(CCH2)(dppe)Cp*]PF6 with nBuLi and phenyl cyanate. The complex behaves as a typical transition metal acetylide upon reaction with tetracyanoethene, a... Read More about The synthesis, structure, reactivity and electrochemical properties of ruthenium complexes featuring cyanoacetylide ligands.

Crystal, Molecular and Electronic Structure of N,N'-diphenyl-N,N'-bis(2,4-dimethylphenyl)-(1,1'-biphenyl)-4,4'-diamine and the Corresponding Radical Cation (2004)
Journal Article
Low, P., Paterson, M., Puschmann, H., Goeta, A., Howard, J., Lambert, C., …Brown, B. (2004). Crystal, Molecular and Electronic Structure of N,N'-diphenyl-N,N'-bis(2,4-dimethylphenyl)-(1,1'-biphenyl)-4,4'-diamine and the Corresponding Radical Cation. Chemistry - A European Journal, 10(1), 83-91. https://doi.org/10.1002/chem.200305200

Oxidation of N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD, 1a) and N,N'-diphenyl-N,N'-bis(2,4-dimethylphenyl)- (1,1'-biphenyl)-4,4'-diamine (1b) with SbCl5 affords the corresponding radical cations quantitatively. The crys... Read More about Crystal, Molecular and Electronic Structure of N,N'-diphenyl-N,N'-bis(2,4-dimethylphenyl)-(1,1'-biphenyl)-4,4'-diamine and the Corresponding Radical Cation.

Cyanoacetylenes and cyanoacetylides: versatile ligands in organometallic chemistry (2003)
Journal Article
Cordiner, R., Corcoran, D., Yufit, D., Goeta, A., Howard, J., & Low, P. (2003). Cyanoacetylenes and cyanoacetylides: versatile ligands in organometallic chemistry. Dalton Transactions, 18, 3541-3549. https://doi.org/10.1039/b306089f

The nitrile like lone pair of the cyanoacetylene PhCequivalent toCCequivalent toN (1) has been found to coordinate readily to the Ru(PPh3)(2)Cp fragment, to give [Ru(Nequivalent toCCequivalent toCPh)(PPh3)(2)Cp]PF6 (2) which may be considered its an... Read More about Cyanoacetylenes and cyanoacetylides: versatile ligands in organometallic chemistry.

Syntheses, Structures, and Spectro-electrochemistry of {Cp*(PP)Ru}C≡CC≡C{Ru(PP)Cp*} (PP = dppm, dppe) and Their Mono- and Dications (2003)
Journal Article
Bruce, M., Ellis, B., Low, P., Skelton, B., & White, A. (2003). Syntheses, Structures, and Spectro-electrochemistry of {Cp*(PP)Ru}C≡CC≡C{Ru(PP)Cp*} (PP = dppm, dppe) and Their Mono- and Dications. Organometallics, 22(16), 3184-3198. https://doi.org/10.1021/om030015g

The complexes {Cp*(PP)Ru}(2)(mu-Cequivalent toCCequivalent toC) (PP = dppm 5a, dppe 5b) have been synthesized from RuCl(PP)Cp* (1a/b) via the corresponding vinylidenes [Ru(=C=CH2)(PP)Cp*](+) (2a/b), deprotonation (KOBut) to the ethynyls Ru(Cequivalen... Read More about Syntheses, Structures, and Spectro-electrochemistry of {Cp*(PP)Ru}C≡CC≡C{Ru(PP)Cp*} (PP = dppm, dppe) and Their Mono- and Dications.

Studies of the S₁ state in a prototypical molecular wire using picosecond time-resolved spectroscopies (2003)
Journal Article
Beeby, A., Findlay, K., Low, P., Marder, T., Matousek, P., Parker, A., Rutter, S., & Towrie, M. (2003). Studies of the S₁ state in a prototypical molecular wire using picosecond time-resolved spectroscopies. Chemical Communications, 2003(19), 2406-2407. https://doi.org/10.1039/b307005k

Picosecond time-resolved resonance Raman spectroscopy, TR3, reveals an intense acetylenic band in the S1 state of the prototypical molecular wire 1,4-bis(phenylethynyl)benzene.

A re-evaluation of the photophysical properties of 1,4-bis(phenylethynyl)benzene: A model for poly(phenyleneethynylene) (2002)
Journal Article
Beeby, A., Findlay, K., Low, P., & Marder, T. (2002). A re-evaluation of the photophysical properties of 1,4-bis(phenylethynyl)benzene: A model for poly(phenyleneethynylene). Journal of the American Chemical Society, 124(28), 8280-8284. https://doi.org/10.1021/ja025568h

Photophysical measurements, recorded in aerated cyclohexane at 283 K, indicate that 1,4-bis-(phenylethynyl) benzene behaves in a conventional manner, undergoing emission from the lowest vibrational level of the first excited singlet state; there is n... Read More about A re-evaluation of the photophysical properties of 1,4-bis(phenylethynyl)benzene: A model for poly(phenyleneethynylene).

Electronic structure of ruthenium(II) polyynyl complexes (2001)
Journal Article
Koentjoro, O., Rousseau, R., & Low, P. (2001). Electronic structure of ruthenium(II) polyynyl complexes. Organometallics, 20(22), 4502-4509. https://doi.org/10.1021/om010304%2B

The electronic structure of the polyynyl complexes [Ru{(C equivalent toC)nR}(PH3)(2)CP] (n = 1-6; R = H, CH3, C6H5, C6H4NH2-P, C6H4NO2-P, CN), the diynyl compounds [Ru{(C equivalent toC)(2)R}CO)(2)CP], and the oxidized species [Ru{(C equivalent toC),... Read More about Electronic structure of ruthenium(II) polyynyl complexes.

Electrochemical evidence for electronic interactions through the para-carborane skeleton in the novel tricluster [{Co2C2(SiMe3)(CO)4(dppm)}2(μ-CB10H10C)] (2001)
Journal Article
Fox, M., Paterson, M., Nervi, C., Galeotti, F., Puschmann, H., Howard, J., & Low, P. (2001). Electrochemical evidence for electronic interactions through the para-carborane skeleton in the novel tricluster [{Co2C2(SiMe3)(CO)4(dppm)}2(μ-CB10H10C)]. Chemical Communications, 2001(17), 1610-1611. https://doi.org/10.1039/b104307m

The electrochemical properties of the title compound reveal electronic interactions between two dicobalt-dicarbon clusters via a 1,12-para-carborane cage.

Photochemistry of the pi-extended 9,10-bis(1,3-dithiol-2- ylidene)-9,10-dihydroanthracene system: Generation and characterisation of the radical cation, dication, and derived products (2001)
Journal Article
Jones, A., Christensen, C., Perepichka, D., Batsanov, A., Beeby, A., Low, P., …Parker, A. (2001). Photochemistry of the pi-extended 9,10-bis(1,3-dithiol-2- ylidene)-9,10-dihydroanthracene system: Generation and characterisation of the radical cation, dication, and derived products. Chemistry - A European Journal, 7(5), 973-978. https://doi.org/10.1002/1521-3765%2820010302%297%3A5%3C973%3A%3Aaid-chem973%3E3.0.co%3B2-%23

Flash photolysis of bis[4,5-di(methylsulfanyl)1,3-dithiol-2- ylidene]-9,10-dihydroanthracene (1) in chloroform leads to formation of the transient radical cation species 1(.+) which has a diagnostic broad absorption band at lambda (max) approximate t... Read More about Photochemistry of the pi-extended 9,10-bis(1,3-dithiol-2- ylidene)-9,10-dihydroanthracene system: Generation and characterisation of the radical cation, dication, and derived products.

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