Nanoscale aryleneethynylene oligomers incorporating fluorenone units as electron-dopable molecular wires

Faraday Discussions
Changsheng WangMartin R Bryce

Abstract

The first general synthetic procedures to obtain fluorenone-containing aryleneethynylene oligomers have been developed. The strategy involves stepwise Sonogashira cross-coupling methodology, with 2,7-diethynylfluorenone and 1,4-diiodo-2,6-di(hexyloxy)benzene building blocks, with terminal benzenethiol functionality protected as cyanoethyl derivatives. A second family of compounds contains a central 9-[(4-pyridyl) methylene]fluorene or 9-[di(4-pyridyl)methylene]fluorene unit in the backbone. UV-Vis absorption studies in solution establish that the increase of molecular lengths ca. 4 nm (compounds 15 and 16) to ca. 7 nm (compounds 17, 27 and 28) results in a very small red shift, with the effective conjugation length slightly longer than that 1,4-di(phenylethynyl)benzene (PEPEP) subunits. The pyridyl groups in 27 and 28 are weakly conjugated to the pi-electron backbone (UV-Vis data) which is consistent with twisted conformation observed in the X-ray crystal structures of model compounds and 24. Cyclic voltammetric studies reveal that the reduction waves of the fluorenone, 9-[(4-pyridyl)methylene]fluorene and 9-[di(4-pyridyl)methylene]fluorene units endow oligomers with n-doping characteristics, with reversible reduction waves bei...Continue Reading

References

Sep 19, 2000·Nature·H ParkP L McEuen
Oct 4, 2000·Physical Review Letters· Di Ventra MN D Lang
Nov 23, 2000·Accounts of Chemical Research·J M Tour
Jan 5, 2002·Chemistry : a European Journal·J M TourI Campbell
Jun 18, 2002·Nature·Jiwoong ParkDaniel C Ralph
Jul 11, 2002·Journal of the American Chemical Society·Andrew BeebyTodd B Marder
Aug 31, 2002·Chemistry : a European Journal·Mogens Brøndsted NielsenFrançois Diederich
Jan 11, 2003·Science·Mark Lundstrom
Apr 10, 2003·Chemical Society Reviews·Neil Robertson, Craig A McGowan
May 8, 2003·Journal of the American Chemical Society·Sandrine FraysseJean-Pierre Launay
May 31, 2003·Science·Abraham Nitzan, Mark A Ratner
Jul 17, 2003·Journal of the American Chemical Society·Naomi P RedmoreMichael J Therien
Oct 23, 2003·Journal of the American Chemical Society·James M TourPaul D Franzon
Dec 11, 2003·Journal of the American Chemical Society·Wolfgang HaissRichard J Nichols
Sep 18, 2004·Angewandte Chemie·Ronald A Wassel, Christopher B Gorman
Sep 24, 2004·Journal of the American Chemical Society·Dennis BongRonald Breslow
Feb 19, 2005·Chemistry : a European Journal·Gregory HoMartin R Bryce
Feb 24, 2005·Journal of the American Chemical Society·Bingqian XuNongjian Tao
Jun 23, 2005·Journal of the American Chemical Society·Xiaoyin XiaoNongjian Tao

❮ Previous
Next ❯

Citations

Apr 4, 2006·Chemical Communications : Chem Comm·Geoffrey J AshwellMartin R Bryce
Nov 17, 2006·Chemical Communications : Chem Comm·Geoffrey J AshwellColin J Lambert
Feb 13, 2013·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Abdelaziz Al OuahabiSylvie Choua
Oct 12, 2012·The Journal of Organic Chemistry·Rajesh KotaDaniell Lewis Mattern
Mar 16, 2017·Macromolecular Rapid Communications·Susanne C SollederMichael A R Meier
Feb 17, 2017·Physical Chemistry Chemical Physics : PCCP·Ali K IsmaelColin J Lambert
Sep 29, 2015·Nature Nanotechnology·Anja WedigIlia Valov

❮ Previous
Next ❯

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.