Document Detail

Convergent synthesis of 10 nm aryleneethynylene molecular wires by an iterative regioselective deprotection/Sonogashira coupling protocol.
MedLine Citation:
PMID:  16388625     Owner:  NLM     Status:  PubMed-not-MEDLINE    
[structure: see text] 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 lambda(max) with increasing molecular length, which approaches saturation at an effective conjugation length of ca. 15-20 pi-units in the molecules, where each phenyl ring or a triple bond is counted as one pi-unit.
Changsheng Wang; Andrei S Batsanov; Martin R Bryce
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  71     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2006 Jan 
Date Detail:
Created Date:  2006-01-03     Completed Date:  2006-07-26     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  108-16     Citation Subset:  -    
Department of Chemistry, University of Durham, Durham DH1 3LE, UK.
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