Synthesis and structural analysis of thiophene-pyrrole-based S,N-heteroacenes

Organic Letters
Christoph WetzelPeter Bäuerle

Abstract

Fused S,N-heterohexacene 4 was synthesized by applying Pd-catalyzed tandem Buchwald-Hartwig coupling and further functionalized to corresponding acceptor-capped derivatives 5 and 6 showing bond length equalization in the π-conjugated backbone and intense optical transitions. Organic thin film transistors (OTFTs) based on a vacuum-deposited film of 6 exhibit p-channel charge-carrier mobilities as high as 0.021 cm(2) V(-1) s(-1) and current on/off ratios of 10(5).

References

Apr 25, 2002·Proceedings of the National Academy of Sciences of the United States of America·J L BrédasJ Cornil
Jul 28, 2005·Journal of the American Chemical Society·Xinnan ZhangAdam J Matzger
Mar 11, 2006·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Frank Würthner, Rüdiger Schmidt
Dec 15, 2006·Chemical Reviews·John E Anthony
May 15, 2010·Angewandte Chemie·Sanjio S Zade, Michael Bendikov
May 19, 2010·Chemistry, an Asian Journal·Ying LiuGui Yu
Aug 16, 2011·Advanced Materials·Kazuo TakimiyaEigo Miyazaki
Mar 17, 2012·Journal of the American Chemical Society·Manuel SchraderDenis Andrienko
Jun 22, 2012·Nature Chemistry·Motonori WatanabeTahsin J Chow
Feb 20, 2013·Angewandte Chemie·Uwe H F BunzManuel Schaffroth
Apr 6, 2013·Journal of the American Chemical Society·Jianguo MeiZhenan Bao
May 1, 2013·Chemical Society Reviews·Wei JiangZhaohui Wang

❮ Previous
Next ❯

Citations

Nov 18, 2015·Journal of Chemical Theory and Computation·Denis JacqueminXavier Blase
Sep 19, 2015·Organic Letters·Koichi MitsudoSeiji Suga
Jul 19, 2016·The Journal of Organic Chemistry·Mariusz Tasior, Daniel T Gryko
Feb 19, 2016·Chemistry : a European Journal·Rafał StężyckiDaniel T Gryko
Mar 10, 2015·Physical Chemistry Chemical Physics : PCCP·Marzena BanasiewiczBolesław Kozankiewicz
Aug 27, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Shumiao ZhangHongjian Sun
Jul 3, 2015·Angewandte Chemie·Christoph WetzelPeter Bäuerle
Jul 6, 2014·Chemistry, an Asian Journal·Anita Janiga, Daniel T Gryko
Apr 18, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Di WuFrançois Mathey
Jul 12, 2019·Beilstein Journal of Organic Chemistry·Pierre-Olivier SchwartzPeter Bäuerle
Jul 23, 2015·Beilstein Journal of Organic Chemistry·Roman A IrgashevValery N Charushin
Jan 29, 2020·Chemistry : a European Journal·Jose S S Neto, Gilson Zeni
Dec 23, 2017·Chemistry, an Asian Journal·Mariusz TasiorDaniel T Gryko
Sep 12, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Rylan M W WolfeSeth C Rasmussen
Feb 19, 2015·The Journal of Organic Chemistry·Maciej Krzeszewski, Daniel T Gryko
Jul 18, 2017·The Journal of Physical Chemistry. B·Alexander RudnickAnna Köhler
Mar 25, 2014·The Journal of Organic Chemistry·Maciej KrzeszewskiDaniel T Gryko

❮ Previous
Next ❯

Related Concepts

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.