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    
Abstract/OtherAbstract:
[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.
Authors:
Changsheng Wang; Andrei S Batsanov; Martin R Bryce
Related Documents :
17696505 - Theoretical studies on structures and spectroscopic properties of a series of novel cat...
14532665 - 2-amino-1,3-benzothiazole-ethyl coumarin-3-carboxylate (1/1).
15817455 - The n-acetyl-d-glucosaminylphosphatidylinositol de-n-acetylase of glycosylphosphatidyli...
18253005 - 4-[2-(3-methoxyphenyl)ethenyl]-n-methylpyridinium tetraphenylborate.
21587695 - Bis(μ-2,4-dihy-droxy-benzoato-κo:o')bis-[aqua-(2,4-dihy-droxy-benzoato-κo)(1,10-phen...
20704295 - Reaction mechanism of ch + c(3)h(6): a theoretical study.
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:  -    
Affiliation:
Department of Chemistry, University of Durham, Durham DH1 3LE, UK.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  Synthesis of 2-amino-8-oxodecanoic acids (Aodas) present in natural hystone deacetylase inhibitors.
Next Document:  Total synthesis and structural elucidation of (-)-maurenone.