Redox properties of non-alternant cyclopenta-fused polycyclic aromatic hydrocarbons: The effect of peripheral pentagon annelation

Koper, Carola; Sarobe, Martín; Jenneskens, Leonardus W.

doi:10.1039/b312234d

Cited by 58 publications

(71 citation statements)

References 44 publications

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“…[3] Due to the remarkable optical [4] and electronic [5] properties of aromatic cyclopentadienides, they show characteristics of alternate PAHs, such as pentacene or hexa-peri-hexabenzocoronenes, that are already being used in organic field-effect transistors (OFETs), [6] organic lightemitting diodes (OLEDs), [7] and organic photovoltaics (OPVs).…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Pentannulation of Polycyclic Aromatic Hydrocarbons

Eversloh

Avlasevich

et al. 2011

Chemistry A European J

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We present a new and versatile one-step synthesis of a series of small molecular chromophores based on cyclopentannulated polycyclic aromatic hydrocarbons (PAH). Easily available pyrene, anthracene, and perylene bromides serve as starting materials for the reactions. The formation of the five-membered ring is achieved by the straightforward palladium(0)-catalyzed carbannulation with various substituted acetylenes. This approach is applicable either to single or multiple annulation procedures leading to hitherto inaccessible PAH topologies. According to the resulting products of the diverse reactions, a mechanistic explanation is proposed. UV/Vis absorption as well as cyclovoltammetric measurements were performed for characterization demonstrating the value of this annulation technique. Optical absorptions of up to 780 nm and absorption coefficients ranging from 8000 to 34,000 M(-1) cm(-1) were detected.

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Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Pentannulation of Polycyclic Aromatic Hydrocarbons

Eversloh

Avlasevich

et al. 2011

Chemistry A European J

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“…less negative first electron reduction potentials (E 1/2 (0/−1) in V versus SCE) [53][54][55]. CP-PAH 3 possesses the least negative first reduction potential E 1/2 (0/−1) of −1.02 V (E 1/2 (0/−1 in V versus SCE: 1, −1.56 V; 2, −1.32 V; 4, −1.15 V (Table 3)), which is exactly in the range found for some bioactive nitro-PAH exhibit- ing direct-acting mutagenic behaviour [49].…”

Section: Direct Mutagenicity Of 2 Andmentioning

confidence: 99%

Bacterial mutagenicity of the three isomeric dicyclopenta-fused pyrenes: the effects of dicyclopenta topology

Otero-Lobato

Jenneskens

Seinen

2004

Mutation Research/Genetic Toxicology and Environmental Mutagene

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Cyclopenta[cd]pyrene (1) and its congeners dicyclopenta [cd,mn]-(2), dicyclopenta [cd,fg]-(3), dicyclopenta [cd,jk]pyrene (4), which were all identified as constituents of combustion exhausts, as well as their partially hydrogenated derivatives 3,4-dihydrocyclopenta[cd]-(5), 1,2,4,5-tetrahydrodicyclopenta[cd,mn]-(6), 5,6,7,8-tetrahydrodicyclopenta[cd,fg]- (7) and 1,2,6,7-tetrahydrodicyclopenta[cd,jk]pyrene (8), were assayed for mutagenicity in the Salmonella typhimurium strain TA98 using different concentrations of microsomal protein in the metabolic activation system (S9-mix, with S9-fraction from liver of Aroclor-1254-treated rats: 2, 4 and 10% (v/v), respectively). Whereas a positive mutagenic response is found for 1-4 in the presence of S9-mix, 5-8 exert no mutagenicity either with or without S9-mix. Since for 1-4 the highest response is observed with S9-mix 2% (v/v) instead of the standard 4% (v/v), a one-step activation pathway, i.e. epoxidation of the five-membered ring olefinic bonds, appears to be operational. Surprisingly, 3 and, to a lesser extent, 2 (11.7 versus 4.2 His revertants/nmol) also give a positive response in the absence of S9-mix. Hence, 2 and 3 are expected to contribute to the direct-acting mutagenicity of the non-polar fraction of combustion exhausts. Presumably for the direct-acting mutagenicity one-electron transfer processes play a role in bioactivation. The experimental observations are supported by semi-empirical AM1 calculations on the possible ultimate metabolites, i.e. mono-epoxides (2a-4a), cis-di-epoxides (2b-4b) and trans-di-epoxides (2c-4c) and the related mono-hydroxy carbocations (2d-4d and 2e-4e), and the radical anions 1 •− -4 •− .

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“…(1) exists between the E 1/2 (0/À1) vs. SCE values of 1-9 [3] and their AEAs ( Table 2). As shown in Fig.…”

Section: åàmentioning

confidence: 99%

“…This stems from their identity as sub-structures of fullerenes and carbon nanotubes [1,2], their potential to show unusual (photo)physical properties, e.g. facile (consecutive) one-electron reduction processes [3], anomalous fluorescence [4] and deviant aromatic character [5], and, their alleged presence (in charged form) in the interstellar medium [6]. In addition, CP-PAHs were found to possess bio-activity [7].…”

Section: Introductionmentioning

confidence: 99%

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Gas phase adiabatic electron affinities of cyclopenta-fused polycyclic aromatic hydrocarbons

Todorov

Koper

Lenthe

et al. 2008

Chemical Physics Letters

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The B3LYP/DZP++ adiabatic electron affinity (AEA) of nine (non)-alternant polycyclic aromatic hydrocarbons are reported and discussed. Calculations became feasible for molecules this size by projecting out the near-linearly dependent part of the one-electron basis. Non-alternant PAH consisting of an alternant PAH core modified by peri-annulation with unsaturated five-membered rings (CP-PAHs) possess markedly enhanced AEAs.

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Redox properties of non-alternant cyclopenta-fused polycyclic aromatic hydrocarbons: The effect of peripheral pentagon annelation

Cited by 58 publications

References 44 publications

Palladium‐Catalyzed Pentannulation of Polycyclic Aromatic Hydrocarbons

Palladium‐Catalyzed Pentannulation of Polycyclic Aromatic Hydrocarbons

Bacterial mutagenicity of the three isomeric dicyclopenta-fused pyrenes: the effects of dicyclopenta topology

Gas phase adiabatic electron affinities of cyclopenta-fused polycyclic aromatic hydrocarbons

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