Electron-Accepting Dithiarubicene (Emeraldicene) and Derivatives Prepared by Unprecedented Nucleophilic Hydrogen Substitution by Alkyllithium Reagents

By understanding the role of DMF as a hydride source via a Pd‐catalyzed reaction and switching to CH3CN solvent, an efficient route for the synthesis of emeraldicene and some new substituted derivatives is reported with potential application in organic electronics. Additionally, the nucleophilic alk...

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Published in:Chemistry : a European journal 2011-02, Vol.17 (9), p.2642-2646
Main Authors: Mohebbi, Ali Reza, Wudl, Fred
Format: Article
Language:English
Subjects:
Alkylation
Chemistry
Crystallization
Derivatives
Electronics
emeraldicene
Heck reaction
Hydrides
nucleophilic aromatic alkylation
organic acceptor
polycyclic heteroaromatic hydrocarbon
Solvents
Stacks
Switching
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cited_by cdi_FETCH-LOGICAL-c5098-a26317f6ca0eb2f1a99d2d5bea4572503269c03f01a7cc7d71205c3313eb1b7f3
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creator Mohebbi, Ali Reza
Wudl, Fred
description By understanding the role of DMF as a hydride source via a Pd‐catalyzed reaction and switching to CH3CN solvent, an efficient route for the synthesis of emeraldicene and some new substituted derivatives is reported with potential application in organic electronics. Additionally, the nucleophilic alkylation of emeraldicene 4 a with alkyllithium reagents provides monosubstituted compounds 7 a and 7 b, the latter crystallizing in columnar stacks, with π–π overlap between adjacent molecules in the stack. Great potential: New derivatives of dithiarubicene (emeraldicene), which are of potential use as organic acceptors, are reported (see figure, R = ‐H, ‐dodecyl, ‐ethylhexyl). Additionally, nucleophilic aromatic hydrogen displacement alkylation of emeraldicene by alkyllithium reagents produced highly soluble mono‐substituted emeraldicene, which crystallized in columnar stacks, with excellent overlap between adjacent molecules in the stack.
doi_str_mv 10.1002/chem.201002608
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source Wiley-Blackwell Read & Publish Collection
subjects Alkylation
Chemistry
Crystallization
Derivatives
Electronics
emeraldicene
Heck reaction
Hydrides
nucleophilic aromatic alkylation
organic acceptor
polycyclic heteroaromatic hydrocarbon
Solvents
Stacks
Switching
title Electron-Accepting Dithiarubicene (Emeraldicene) and Derivatives Prepared by Unprecedented Nucleophilic Hydrogen Substitution by Alkyllithium Reagents
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