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Literature DB >> 17109533

Oligoindenopyrenes: a new class of polycyclic aromatics.

Hermann A Wegner¹, Helge Reisch, Karsten Rauch, Attila Demeter, Klaas A Zachariasse, Armin de Meijere, Lawrence T Scott.

Abstract

A new class of polycyclic aromatic hydrocarbons--oligoindenopyrenes--has been synthesized featuring a Pd-catalyzed Suzuki-Heck coupling cascade. The oligoindenopyrenes are robust, highly colored substructures of C(70) and have properties that might prove useful in new organic materials or devices. After excitation, the tetraindenopyrene derivative 3d undergoes efficient deactivation (99%) by internal conversion to the ground state. The small fluorescence quantum yield (0.004) is in accordance with the short (0.6 ns) fluorescence decay time.

Entities: Chemical

Mesh：

Substances：
Pyrenes

Year: 2006 PMID： 17109533 DOI： 10.1021/jo0613939

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

6 in total

1. Preparation of chiral-at-metal catalysts and their use in asymmetric photoredox chemistry.

Authors: Jiajia Ma; Xiao Zhang; Xiaoqiang Huang; Shipeng Luo; Eric Meggers
Journal: Nat Protoc Date: 2018-03-01 Impact factor: 13.491

2. Synthesis of ¹³C₄-labelled oxidized metabolites of the carcinogenic polycyclic aromatic hydrocarbon benzo[a]pyrene.

Authors: Anhui Wu; Daiwang Xu; Ding Lu; Trevor M Penning; Ian A Blair; Ronald G Harvey
Journal: Tetrahedron Date: 2012-09-01 Impact factor: 2.457

3. An Electron-Poor C64 Nanographene by Palladium-Catalyzed Cascade C-C Bond Formation: One-Pot Synthesis and Single-Crystal Structure Analysis.

Authors: Sabine Seifert; Kazutaka Shoyama; David Schmidt; Frank Würthner
Journal: Angew Chem Int Ed Engl Date: 2016-04-05 Impact factor: 15.336

Oligoindenopyrenes: a new class of polycyclic aromatics.

1. Preparation of chiral-at-metal catalysts and their use in asymmetric photoredox chemistry.

2. Synthesis of ¹³C₄-labelled oxidized metabolites of the carcinogenic polycyclic aromatic hydrocarbon benzo[a]pyrene.

3. An Electron-Poor C64 Nanographene by Palladium-Catalyzed Cascade C-C Bond Formation: One-Pot Synthesis and Single-Crystal Structure Analysis.

4. Acenaphthenoannulation Induced by the Dual Lewis Acidity of Alumina.

5. One-pot synthesis of dicyclopenta-fused peropyrene via a fourfold alkyne annulation.

6. as-Indaceno[3,2,1,8,7,6-ghijklm]terrylene as a near-infrared absorbing C₇₀-fragment.

Oligoindenopyrenes: a new class of polycyclic aromatics.

1. Preparation of chiral-at-metal catalysts and their use in asymmetric photoredox chemistry.

2. Synthesis of 13C4-labelled oxidized metabolites of the carcinogenic polycyclic aromatic hydrocarbon benzo[a]pyrene.

3. An Electron-Poor C64 Nanographene by Palladium-Catalyzed Cascade C-C Bond Formation: One-Pot Synthesis and Single-Crystal Structure Analysis.

4. Acenaphthenoannulation Induced by the Dual Lewis Acidity of Alumina.

5. One-pot synthesis of dicyclopenta-fused peropyrene via a fourfold alkyne annulation.

6. as-Indaceno[3,2,1,8,7,6-ghijklm]terrylene as a near-infrared absorbing C70-fragment.

2. Synthesis of ¹³C₄-labelled oxidized metabolites of the carcinogenic polycyclic aromatic hydrocarbon benzo[a]pyrene.

6. as-Indaceno[3,2,1,8,7,6-ghijklm]terrylene as a near-infrared absorbing C₇₀-fragment.