Potassium salt promoted regioselective three-component coupling synthesis of 1,4-asymmetrical [60]fullerene bisadducts with superior electron transport properties

Chemical Communications : Chem Comm
Fei LiShangfeng Yang

Abstract

An efficient one-pot three-component domino coupling reaction of phenols, C60, and bromoalkanes was developed, resulting in the highly regioselective synthesis of 1,4-asymmetrical C60 bisadducts. The reaction utilizes KOtBu as a promoter and likely proceeds by an oxyanion/carbanion rearrangement/nucleophilic addition cascade. This new methodology is particularly effective for the synthesis of 1,4-asymmetrical C60 electron transport materials. Its utility is demonstrated by the synthesis of a new efficient 1,4-C60 ETM, which possesses better performance, easier synthesis, and a lower cost compared with the commercially available PCBM.

References

Mar 6, 2003·Journal of the American Chemical Society·Eiichi NakamuraMasaya Sawamura
Nov 19, 2003·Accounts of Chemical Research·Eiichi Nakamura, Hiroyuki Isobe
Mar 12, 2005·The Journal of Organic Chemistry·Zhong-Xiu Chen, Guan-Wu Wang
May 17, 2006·Chemical Communications : Chem Comm·Nazario Martín
Jul 14, 2006·Organic Letters·Yusuke TajimaKazuo Takeuchi
Dec 15, 2006·Chemical Reviews·Carlo Thilgen, François Diederich
Dec 15, 2006·Chemical Reviews·Francesco Giacalone, Nazario Martín
Jun 15, 2007·Journal of the American Chemical Society·Masakazu NamboKenichiro Itami
Jul 26, 2008·Chemical Reviews·Yutaka Matsuo, Eiichi Nakamura
Mar 7, 2009·Organic Letters·Guan-Wu WangZhong-Xiu Chen
Jul 10, 2009·Chemical Society Reviews·Dirk M GuldiNazario Martín
Nov 19, 2009·Journal of the American Chemical Society·Masakazu NamboKenichiro Itami
Aug 19, 2010·Journal of the American Chemical Society·Zuo XiaoEiichi Nakamura
Feb 10, 2011·Journal of the American Chemical Society·Masakazu NamboKenichiro Itami
Jul 13, 2011·Journal of the American Chemical Society·Shirong LuYoshinori Yamamoto
Sep 8, 2011·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Kenichiro Itami
Apr 11, 2013·Chemical Reviews·Manolis D Tzirakis, Michael Orfanopoulos
Feb 4, 2014·Journal of the American Chemical Society·Juan Marco-MartínezNazario Martín
Aug 1, 2014·Accounts of Chemical Research·Enrique E MarotoNazario Martín
Oct 28, 2014·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Liangbing Gan
Nov 5, 2014·Chemical Communications : Chem Comm·Weili SiTienan Jin
Jan 15, 2015·Organic Letters·Yanbang LiLiangbing Gan
Mar 15, 2015·Chemical Communications : Chem Comm·Weili SiTienan Jin
Nov 26, 2015·Journal of the American Chemical Society·Yaowen LiYang Yang
Nov 5, 2016·The Journal of Physical Chemistry Letters·Marta Valles-PelardaIvan Mora-Sero
Jan 24, 2017·Chemical Communications : Chem Comm·Fei LiGuan-Wu Wang
Dec 12, 2017·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Edison CastroLuis Echegoyen
Jul 19, 2019·Accounts of Chemical Research·Tomokazu Umeyama, Hiroshi Imahori

❮ Previous
Next ❯

Methods Mentioned

BETA
column chromatography
X-ray
atomic force microscopy

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.