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

Reference:

Khan, M. S., Al-Mandhary, M. R. A., Al-Suti, M. K., Ahrens, B., Mahon, M. F., Male, L., Raithby, P. R., Boothby, C. E. and Kohler, A., 2003. Synthesis, characterisation and optical spectroscopy of diynes and poly-ynes containing derivatised fluorenes in the backbone. Dalton Transactions

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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-dioctyl uorene 1a, 2-ethynyl-9,9-dioctyl uorene 1b, 2,7-bis(trimethylsilylethynyl)-9,9-dioctyluorene 2a, 2,7-bis(ethynyl)-9,9-dioctyl uorene 2b, have been synthesised. Reaction of trans-[((PBu3)-Bu-n)(2)PtCl2] with 2 equivalents of the terminal ethyne 1b yields the mononuclear platinum(II) diyne 3, reaction of trans-[(Ph)(Et3P)(2) PtCl] with 0.5 equivalents of the diterminal ethyne 2b gives the dinuclear platinum(II) diyne 4 while 1 : 1 reaction between trans-[((PBu3)-Bu-n)(2)PtCl2] 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) uorene 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.

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