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Issue 1, 2003
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Synthesis, characterisation and optical spectroscopy of diynes and poly-ynes containing derivatised fluorenes in the backbone

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Abstract

A series of trimethylsilyl-protected and terminal mono- and bis-alkynes based on 9,9-dioctylfluorene, 2-(trimethylsilylethynyl)-9,9-dioctylfluorene 1a, 2-ethynyl-9,9-dioctylfluorene 1b, 2,7-bis(trimethylsilylethynyl)-9,9-dioctylfluorene 2a, 2,7-bis(ethynyl)-9,9-dioctylfluorene 2b, have been synthesised. Reaction of trans-[(PnBu3)2PtCl2] with 2 equivalents of the terminal ethyne 1b yields the mononuclear platinum(II) diyne 3, reaction of trans-[(Ph)(Et3P)2PtCl] with 0.5 equivalents of the diterminal ethyne 2b gives the dinuclear platinum(II) diyne 4 while 1 ∶ 1 reaction between trans-[(PnBu3)2PtCl2] and 2b gives the platinum(II) poly-yne 5. Treatment of 2,5-dioctyloxy-1,4-diiodobenzene with 1b in 1 ∶ 2 stoichiometry produces the organic di-yne 6 while 1 ∶ 1 reaction between 2,5-dioctyloxy-1,4-diiodobenzene and 2b, 2,7-bis(ethynyl)fluorene or 2,7-bis(ethynyl)fluoren-9-one produces the organic co-poly-ynes 7–9. All the new materials have been characterised by analytical and spectroscopic methods and the single crystal X-ray structures of 2a and 3 have been determined. The diynes and poly-ynes are soluble in organic solvents and are readily cast into thin films. Optical spectroscopic measurements reveal that the attachment of octyl side-chains on the fluorenyl spacer reduces inter-chain interaction in the poly-ynes while a fluorenonyl spacer creates a donor–acceptor interaction along the rigid backbone of the organometallic poly-ynes and organic co-poly-ynes.

Graphical abstract: Synthesis, characterisation and optical spectroscopy of diynes and poly-ynes containing derivatised fluorenes in the backbone

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Publication details

The article was received on 17 Sep 2002, accepted on 24 Oct 2002 and first published on 25 Nov 2002


Article type: Paper
DOI: 10.1039/B208963G
Dalton Trans., 2003, 74-84

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    Synthesis, characterisation and optical spectroscopy of diynes and poly-ynes containing derivatised fluorenes in the backbone

    M. S. Khan, M. R. A. Al-Mandhary, M. K. Al-Suti, B. Ahrens, M. F. Mahon, L. Male, P. R. Raithby, C. E. Boothby and A. Köhler, Dalton Trans., 2003, 74
    DOI: 10.1039/B208963G

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