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Chempluschem

Title:		"Reductive Aromatization/Dearomatization and Elimination Reactions to Access Conjugated Polycyclic Hydrocarbons, Heteroacenes, and Cumulenes"
Author(s):		Marshall JL; Lehnherr D; Lindner BD; Tykwinski RR;
Address:		"Department of Chemistry, Gunning-Lemieux Chemistry Center, University of Alberta, Edmonton, AB, T6G 2G2, Canada. Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY, 14853, USA. Department for Chemistry and Pharmacy, and Interdisciplinary Center for Molecular Materials (ICCM), Friedrich-Alexander-Universitat Erlangen-Nurnberg (FAU), Henkestrasse 42, 91054, Erlangen, Germany"
Journal Title:		Chempluschem
Year:		2017
Volume:		82
Issue:		7
Page Number:		967 - 1001
DOI:		10.1002/cplu.201700168
ISSN/ISBN:		2192-6506 (Electronic) 2192-6506 (Linking)
Abstract:		"Acenes, heteroacenes, conjugated polycyclic hydrocarbons, and polycyclic aromatic hydrocarbons (collectively referred to in this review as conjugated polycyclic molecules, CPMs) have fascinated chemists since they were first isolated and synthesized in the mid 19th century. Most recently, these compounds have shown significant promise as the active components in organic devices (e.g., solar cells, thin-film transistors, light-emitting diodes, etc.), and, since 2001, a plethora of publications detail synthetic strategies to produce CPMs. In this review, we discuss reductive aromatization, reductive dearomatization, and elimination/extrusion reactions used to form CPMs. After a brief discussion on early methods to synthesize CPMs, we detail the use of reagents used for the reductive (de)aromatization of precursors containing 1,4-diols/diethers, including SnCl(2) and iodide (I(-) ). Extension of these methods to carbomers and cumulenes is briefly discussed. We then describe low-valent metal species used to reduce endoxides to CPMs, and discuss the methods to directly reduce acenediones and acenones to the respective acene. In the final section, we describe methods used to affect aromatization to the desired CPM via extrusion of small, volatile molecules"
Keywords:		acenes cumulenes indenofluorenes polycyclic aromatic hydrocarbons reductive elimination;
Notes:		"PubMed-not-MEDLINEMarshall, Jonathan L Lehnherr, Dan Lindner, Benjamin D Tykwinski, Rik R eng SFB 953, ''Synthetic Carbon Allotropes''/Deutsche Forschungsgemeinschaft/ Cluster of Excellence ''Engineering of Advanced Materials''/Deutsche Forschungsgemeinschaft/ Solar Technologies go Hybrid/Bavarian State Ministry for Science, Research and Art/ Review Germany 2017/07/01 Chempluschem. 2017 Jul; 82(7):967-1001. doi: 10.1002/cplu.201700168"