Acenes with a click

Waterloo A, Kunakom S, Hampel F, Tykwinski R (2012)


Publication Type: Journal article, Original article

Publication year: 2012

Journal

Original Authors: Waterloo A.R., Kunakom S., Hampel F., Tykwinski R.R.

Publisher: Wiley-VCH Verlag

Book Volume: 213

Pages Range: 1020-1032

DOI: 10.1002/macp.201100622

Abstract

A protected pentacene precursor is functionalized in the 6- and 13-positions with alkyne groups and subsequently derivatized by a copper-catalyzed azide-alkyne Huisgen cycloaddition (CuAAC) reaction. Aromatization then gives the desired pentacene derivatives. This method offers an expedient route to a range of bench-top stable, pentacene, and oligopentacene based chromophores, all derived from a single building block. These new pentacene derivatives are characterized by NMR, IR, and UV-Vis spectroscopies. X-ray crystallographic data for two derivatives is used to evaluate the prospect of electronic communication in the solid state via π-stacking interactions. Full Paper: The CuAAC reaction of azides with a protected pentacene precursor is developed to formally establish compatibility of this powerful reaction with the conjugated pentacene chromophore. Alkyl, aryl, heteroaryl, and oligomeric azides are successfully used. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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How to cite

APA:

Waterloo, A., Kunakom, S., Hampel, F., & Tykwinski, R. (2012). Acenes with a click. Macromolecular Chemistry and Physics, 213, 1020-1032. https://doi.org/10.1002/macp.201100622

MLA:

Waterloo, Andreas, et al. "Acenes with a click." Macromolecular Chemistry and Physics 213 (2012): 1020-1032.

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