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Convergent synthesis of 10 nm aryleethynylene molecular wires by an iterative regioselective deprotection/sonogashira coupling protocol.

Wang, C. and Batsanov, A. S. and Bryce, M. R. (2006) 'Convergent synthesis of 10 nm aryleethynylene molecular wires by an iterative regioselective deprotection/sonogashira coupling protocol.', Journal of organic chemistry., 71 (1). pp. 108-116.

Abstract

The synthesis of a new series of rigid-rod aryleneethynylene derivatives of up to ca. 10 nm molecular length (compounds 16 and 17) is reported using iterative Pd-mediated Sonogashira coupling methodology combined with regioselective removal of the different protecting groups (namely, trimethylsilyl and 2-hydroxyprop-2-yl groups) from the terminal alkyne units. Additionally, the TMS-acetylene unit has been cleanly deprotected to afford a terminal alkyne in the presence of a cyanoethylsulfanyl group. Some of these molecular wires are functionalized with terminal protected thiophenol units for attachment to metal surfaces (compounds 16 and 17). Internal electron-acceptor units have been incorporated into their structures, namely, 9-[di(4-pyridyl)methylene]fluorene (compound 17) or fluorenone (compounds 19-22). Optical absorption and photoluminescence spectra reveal a red shift in the value of max with increasing molecular length, which approaches saturation at an effective conjugation length of ca. 15-20 -units in the molecules, where each phenyl ring or a triple bond is counted as one -unit.

Item Type:Article
Additional Information:
Full text:Full text not available from this repository.
Publisher Web site:http://dx.doi.org/10.1021/jo051711o
Record Created:25 Apr 2007
Last Modified:08 Apr 2009 16:30

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