Electron transfer in polyaromatic hydrocarbons and molecular carbon nanostructures

Ripani, Lorenzo; Bombonato, Elena; Paolucci, Francesco; Marcaccio, Massimo

doi:10.1016/j.coelec.2022.101065

Cited by 4 publications

(2 citation statements)

References 74 publications

(99 reference statements)

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“…Herein, we provide a survey on electrochemical syntheses of PAHs largely by hydrogen evolution reaction (HER), with a focus on recent trends and developments until January 2023. While PAHs were defined as π ‐conjugated molecules containing three or more condensed aromatic rings, [ 47 ] we will shed light on the syntheses of molecules that have proven useful, or bear unique potential for material sciences. The individual sections of the review are structured into two sections of direct electrolysis and indirect electrolysis.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Syntheses of Polycyclic Aromatic Hydrocarbons (PAHs)

2023

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Polycyclic aromatic hydrocarbons (PAHs) have surfaced as increasingly viable components in optoelectronics and material sciences. The development of highly efficient and atom‐economic tools to prepare PAHs under exceedingly mild conditions constitutes a long‐term goal. Traditional syntheses of PAHs have largely relied on multistep approaches or the conventional Scholl reaction. However, Scholl reactions are largely inefficient with electron‐deficient substrates, require stoichiometric chemical oxidants, and typically occur in the presence of strong acid. In sharp contrast, electrochemistry has gained considerable momentum during the past decade as an alternative for the facile and straightforward PAHs assembly, generally via electro‐oxidative dehydrogenative annulation, releasing molecular hydrogen as the sole stoichiometric byproduct by the hydrogen evolution reaction (HER). This review provides an overview on the recent and significant advances in the field of electrochemical syntheses of various PAHs until January 2023.This article is protected by copyright. All rights reserved

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Section: Introductionmentioning

confidence: 99%

Electrochemical Syntheses of Polycyclic Aromatic Hydrocarbons (PAHs)

2023

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“…11,12 Furthermore, substituting the PAH core with 3-D chromophores would inhibit the aggregation and improve their solubility to prepare light harvesting molecules and enable exploitation of the photon capturing capabilities. 13 Among various planar PAHs known-to-date, naphthalene and pyrene are widely studied chromophores due to their high chemical stability and exciting optical and electrochemical properties. 9,14,15 Naphthalene is a bulky electron-rich unit which can be easily functionalized at 1,2-positions, and when connected to other chromophores it participates in either PET or PEnT processes.…”

Section: Introductionmentioning

confidence: 99%

Excitation wavelength-reliant light-induced energy and electron processes in pyrene and naphthalene functionalized dual-dye integrated polyaromatic azaborondipyrromethenes

Boligorla,

Rajesh,

Giribabu

et al. 2023

New J. Chem.

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Catalytic Cycloisomerization of Enyne Diesters Derived from Biaryls and Related Substrates

et al. 2023

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Enyne diesters derived from biaryls and related substrates undergo intramolecular [2 + 2]cycloaddition and concomitant cyclo-reversion when treated with 10 mol% In(OTf) 3 in 1,2-dichloroethane. This enyne metathesis type cycloisomerization reaction enables the synthesis of phenanthrene, benzophenanthrene, benzotetraphene and other polycyclic (hetero)aromatic compounds bearing a synthetically useful diethyl β-(hetero)arylidene malonate moiety in a step-and atom-economic manner. In(OTf) 3 -catalyzed two independent intramolecular cycloisomerization on substrates 5 a and 5 b provides direct access to benzotetraphenes 6 a and 6 b containing bis(diethyl β-phenylmethylene malonate) moiety. Tetrasubstituted vinylidene malonate 4 a, substiututed by two different aromatic groups, is stereoselectively converted into Eand Z-isomer of triaryl group containing all carbon tetrasubstituted olefins (8 a, 8 a' and 8 b) via Pd-catalyzed stereoselective decarboxylative arylation reaction.

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Electron transfer in polyaromatic hydrocarbons and molecular carbon nanostructures

Cited by 4 publications

References 74 publications

Electrochemical Syntheses of Polycyclic Aromatic Hydrocarbons (PAHs)

Electrochemical Syntheses of Polycyclic Aromatic Hydrocarbons (PAHs)

Excitation wavelength-reliant light-induced energy and electron processes in pyrene and naphthalene functionalized dual-dye integrated polyaromatic azaborondipyrromethenes

Catalytic Cycloisomerization of Enyne Diesters Derived from Biaryls and Related Substrates

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