Electroreduction of organic compounds. 28. Partial Hydrogenation of Polycyclic Aromatic Hydrocarbons by electroreduction in protic solvents

Anowski, S.; Voß, Jürgen

doi:10.1002/prac.19963380166

Cited by 8 publications

(3 citation statements)

References 10 publications

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“…The E 0.0 transition of the open DTEP unit was deduced analogously from the spectra of dyad 1a (Figure , top) (25400 cm -1 ≙ 3.15 eV), while that of the closed DTEP unit was derived from the difference of the corresponding redox potentials of 2b (1.51 eV ≙ 12180 cm -1 ), since no emission could be detected in this case. It is noteworthy that the potential for the reduction of the anthracene unit (−2.26 V) obtained by summing up the E 0.0 transition and the approximate HOMO energy of anthracene is in good agreement with literature data …”

Section: Resultssupporting

confidence: 87%

Optical ON/OFF Switching of Intramolecular Photoinduced Charge Separation in a Donor−Bridge−Acceptor System Containing Dithienylethene

et al. 2000

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In the newly designed photoswitchable electron transfer compound 2, our previously published donor−bridge−acceptor system (anthracene−CH2−bithiophene−pyridinium) is modified by incorporation of the photoisomerizable dithienylethene (DTE) as a switching unit. In the open-ring form 2a, excitation of the anthracene donor leads to an intramolecular charge separation proved by identification of the anthracene radical cation in transient absorption spectra (ON state). After photocyclization to the closed-ring isomer (2a → 2b), the intramolecular charge separation is completely suppressed (OFF state). The reversibility of the ON/OFF switching is verified. From UV−vis absorption spectra and cyclovoltammetric studies it is deduced that in the open-ring isomer 2a (ON state) conjugation is markedly restricted within the dithienylethene bridge, whereas in the closed-ring isomer 2b (OFF state) the conjugation is extended over the whole dithienylethenepyridinium (DTEP) subunit. Consequently, in 2 an enlarged conjugation within the bridge is not decisive for photoinduced charge separation. Instead the observed transfer properties can be understood by thermodynamic aspects.

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Section: Resultssupporting

confidence: 87%

Optical ON/OFF Switching of Intramolecular Photoinduced Charge Separation in a Donor−Bridge−Acceptor System Containing Dithienylethene

et al. 2000

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“…In a context of selective polyaromatic reductions, [51][52][53][54][55][56] these ideas should not be limited to the above series. Restricting ourselves to D 3h symmetries, let us consider coronene 4 a. Saturating six peripheral atoms at appropriate positions will transform it into an hexa-substituted benzene 4, which has a septet ground state in which six unpaired electrons of the same color spread on 18 conjugated carbons, conferring a density of parallel spins as high as 1/3.…”

Section: Qualitative Conception From Fused Polyaromatic Moleculesmentioning

confidence: 99%

“…In a context of selective polyaromatic reductions,51–56 these ideas should not be limited to the above series. Restricting ourselves to D 3 h symmetries, let us consider coronene 4 a .…”

Section: Introductionmentioning

confidence: 99%

Theoretical Design of High‐Spin Polycyclic Hydrocarbons

Trinquier¹,

Suaud²,

Malrieu³

2010

Chemistry A European J

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High-spin organic structures can be obtained from fused polycyclic hydrocarbons, by converting selected peripheral HC(sp(2)) sites into H(2)C(sp(3)) ones, guided by Ovchinnikov's rule. Theoretical investigation is performed on a few examples of such systems, involving three to twelve fused rings, and maintaining threefold symmetry. Unrestricted DFT (UDFT) calculations, including geometry optimizations, confirm the high-spin multiplicity of the ground state. Spin-density distributions and low-energy spectra are further studied through geometry-dependent Heisenberg-Hamiltonian diagonalizations and explicit correlated ab initio treatments, which all agree on the high-spin character of the suggested structures, and locate the low-lying states at significantly higher energies. In particular, the lowest-lying state of lower multiplicity is always found to be higher than kT at room temperature (at least ten times higher). Simplification of the ferromagnetic organization based on sets of semilocalized nonbonding orbitals is proposed. Molecular architectures are thus conceived in which the ferromagnetically-coupled unpaired electrons tally up to one third of the involved conjugated carbons. Connecting such building blocks should provide bidimensional materials endowed with robust magnetic properties.

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Formation of Alkanes and Arenes by Reduction

Larock

Zhang

2017

Comprehensive Organic Transformations

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Cyclic Alkanes Arenes Alkenes Alkynes Organic Halides Amines and Derivatives Nitro Compounds Ethers Alcohols and Phenols Sulfur Compounds Selenium and Tellurium Compounds Aldehydes and Ketones Acetals Carboxylic Acids Acid Halides Anhydrides Esters and Lactones Nitriles Isonitriles

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Electroreduction of organic compounds. 28. Partial Hydrogenation of Polycyclic Aromatic Hydrocarbons by electroreduction in protic solvents

Cited by 8 publications

References 10 publications

Optical ON/OFF Switching of Intramolecular Photoinduced Charge Separation in a Donor−Bridge−Acceptor System Containing Dithienylethene

Optical ON/OFF Switching of Intramolecular Photoinduced Charge Separation in a Donor−Bridge−Acceptor System Containing Dithienylethene

Theoretical Design of High‐Spin Polycyclic Hydrocarbons

Formation of Alkanes and Arenes by Reduction

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