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Synthesis, optical properties, crystal structures and phase behaviour of selectively fluorinated 1,4-bis(4′-pyridylethynyl)benzenes, 4-(phenylethynyl)pyridines and 9,10-bis(4′-pyridylethynyl)-anthracene, and a Zn(NO3)2 coordination polymer

Lookup NU author(s): Dr Donocadh Lydon, Emeritus Professor Bill Clegg, Professor Todd Marder

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Abstract

A series of selectively fluorinated and non-fluorinated rigid rods based on the 4-pyridylethynyl group, namely 1,4-bis(4′-pyridylethynyl)benzene (1a), 1,4-bis(4′-pyridylethynyl)tetrafluorobenzene (1b), 1,4-bis(2′,3′,5′,6′-tetrafluoropyridylethynyl)benzene (1c), 1,4-bis(2′,3′,5′,6′-tetrafluoropyridylethynyl) tetrafluorobenzene (1d), 9,10-bis(4′-pyridylethynyl)anthracene (2), 4-(pentafluorophenylethynyl)pyridine (3a) and 4-(phenylethynyl)- tetrafluoropyridine (3b) were prepared in good yields using Pd/Cu-catalysed Sonogashira cross-coupling reactions and/or lithium chemistry involving nucleophilic aromatic substitution. UV-Vis absorption and fluorescence spectra for 1a-d and 2 are reported. The X-ray crystal structures of 1b, 1c, 2, 3a and 3b show a variety of packing motifs, none of which involve arene-perfluoroarene stacking. The phase behaviour of 1a-1c has been studied by differential thermal analysis and transmitted polarised light microscopy. Compound 1b exhibits an ordered phase between 227.6 and 272.5 °C which is either hexatic B or crystal B. A 1:1 complex (4) between 1b and Zn(NO3)2 has been prepared; its crystal structure consists of zig-zag polymer chains held together by hydrogen bonds.


Publication metadata

Author(s): Fasina TM, Collings JC, Lydon DP, Albesa-Jove D, Batsanov AS, Howard JAK, Nguyen P, Bruce M, Scott AJ, Clegg W, Watt SW, Viney C, Marder TB

Publication type: Article

Publication status: Published

Journal: Journal of Materials Chemistry

Year: 2004

Volume: 14

Issue: 15

Pages: 2395-2404

ISSN (print): 0959-9428

ISSN (electronic): 1364-5501

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/b405128a

DOI: 10.1039/b405128a


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