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A Practical and Efficient Synthesis of Uniform Conjugated Rod‐Like Oligomers

Hahn, Daniel 1,2; Schneider, Rebekka V. 1,2; Foitzik, Elena 1,2; Meier, Michael A. R. 1,2
1 Laboratorium für Applikationen der Synchrotronstrahlung (LAS), Karlsruher Institut für Technologie (KIT)
2 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)

Abstract:

Herein, a more practical and efficient synthesis protocol for the preparation of uniform rod-like oligo(1,4-phenylene ethynylene)s (OPE)s is presented. Applying an iterative reaction cycle consisting of a decarboxylative coupling reaction and a saponification of an alkynyl carboxylic ester, a uniform pentamer is obtained in ten steps with 14% overall yield. The copper-free conditions prevent homocoupling until the trimer stage, resulting in a significantly easier work-up of the products. Homocoupling is observed from the tetramer stage on, but a simple variation of the work-up procedure also yields the uniform tetramer and pentamer. A thorough comparison with the commonly used and described Sonogashira approach reveals that with the new presented strategy, OPEs can be built in similar overall yield, but easier purification and in a quarter of the time. All oligomers are fully characterized by proton and carbon nuclear magnetic resonance spectroscopy (NMR), mass spectrometry (MS), size-exclusion chromatography (SEC), and infrared spectroscopy (IR).


Verlagsausgabe §
DOI: 10.5445/IR/1000135096
Veröffentlicht am 07.07.2021
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische und Chemische Systeme (IBCS)
Publikationstyp Zeitschriftenaufsatz
Publikationsmonat/-jahr 05.2021
Sprache Englisch
Identifikator ISSN: 1022-1336, 1521-3927
KITopen-ID: 1000135096
HGF-Programm 43.33.11 (POF IV, LK 01) Adaptive and Bioinstructive Materials Systems
Erschienen in Macromolecular rapid communications
Verlag John Wiley and Sons
Band 42
Heft 9
Seiten Art.Nr.: 2000735
Vorab online veröffentlicht am 01.03.2021
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