Synthesis and Size-Dependent Properties of [12], [16], and [24]Carbon Nanobelts

Journal of the American Chemical Society
Guillaume PovieKenichiro Itami

Abstract

The synthesis and X-ray crystal structure of the first member of the carbon nanobelt family is reported. [12]Carbon nanobelt ([12]CNB) was originally obtained from a nickel-mediated reductive coupling reaction of a dodecabrominated macrocyclic precursor, albeit only in 1% yield. The present article reports on the development of this synthetic strategy and its extension to the preparation of the [16] and [24]CNB analogues. In particular, our extensive investigations on the final belt-forming, nickel-mediated reaction led to the development of a new ligand system that provides [12]CNB in up to 7% yield, contributing to the commercialization of [12]CNB. The belt structures of [12], [16], and [24]CNB were characterized by NMR, UV-vis, and Raman spectroscopy as well as mass spectrometry and X-ray crystallography. The fluorescence of the CNBs in solution displayed a remarkable dependence on the ring size, ranging from a broad red emission ([12]CNB) to a narrow-band blue emission ([24]CNB), while both features are observed for [16]CNB.

References

Feb 19, 2002·Chemical Reviews·P. M. Ajayan
Feb 23, 2002·Science·Lawrence T ScottArmin de Meijere
Mar 6, 2003·Journal of the American Chemical Society·Eiichi NakamuraMasaya Sawamura
Jul 18, 2003·Chemistry : a European Journal·Wolf Dietrich NeudorffA Dieter Schlüter
Sep 23, 2003·Angewandte Chemie·Lawrence T Scott
May 8, 2008·Journal of the American Chemical Society·Birgit EsserRolf Gleiter
Dec 3, 2011·Journal of the American Chemical Society·Lawrence T ScottBo Li
Mar 24, 2012·Organic & Biomolecular Chemistry·Yasutomo SegawaKenichiro Itami
Sep 28, 2012·Physical Chemistry Chemical Physics : PCCP·Mamoru FujitsukaTetsuro Majima
Dec 21, 2012·Angewandte Chemie·Damian Myśliwiec, Marcin Stępień
Jun 22, 2013·Nature Chemistry·Haruka OmachiKenichiro Itami
Oct 11, 2013·Chemistry : a European Journal·Takahiro IwamotoShigeru Yamago
Jan 23, 2014·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Shigeru YamagoTakahiro Iwamoto
Jan 24, 2014·Angewandte Chemie·Florian E GollingKlaus Müllen
Jan 28, 2014·Journal of the American Chemical Society·Eiichi KayaharaShigeru Yamago
Mar 13, 2014·Angewandte Chemie·Yusuke NakanishiHisanori Shinohara
Sep 17, 2014·Chemistry : a European Journal·Takahiro IwamotoShigeru Yamago
Dec 30, 2014·Journal of the American Chemical Society·Damian MyśliwiecMarcin Stępień
Feb 18, 2015·Accounts of Chemical Research·Matthew R Golder, Ramesh Jasti
Mar 5, 2015·Chemical Society Reviews·Simon E Lewis
Apr 29, 2015·Chemical Society Reviews·Evan R Darzi, Ramesh Jasti
May 15, 2015·The Journal of Organic Chemistry·Damian MyśliwiecMarcin Stępień
Sep 9, 2015·Chemical Communications : Chem Comm·Marcin A MajewskiMarcin Stępień
Oct 8, 2013·Journal of Chemical Theory and Computation·Agisilaos ChantzisDenis Jacquemin
Feb 19, 2016·Angewandte Chemie·Yasutomo SegawaKenichiro Itami
May 3, 2016·Journal of the American Chemical Society·Matthew R GolderRamesh Jasti
May 4, 2016·Chemistry, an Asian Journal·Eiichi KayaharaShigeru Yamago
Oct 30, 2016·Angewandte Chemie·Marcin A MajewskiMarcin Stępień
Apr 15, 2017·Science·Guillaume PovieKenichiro Itami
Jul 1, 2017·ChemPlusChem·Sigma HashimotoShigeru Yamago

❮ Previous
Next ❯

Citations

Jan 29, 2019·Chemistry : a European Journal·Shinji Toyota, Eiji Tsurumaki
Apr 27, 2019·Angewandte Chemie·Fabian SchulzDiego Peña
Aug 25, 2019·Nature Communications·Shinya AdachiNaoya Kumagai
May 22, 2020·Angewandte Chemie·Zhouyang LuoDahui Zhao
Jan 15, 2019·Physical Chemistry Chemical Physics : PCCP·Sofia CanolaFabrizia Negri
Sep 3, 2020·Chemical Science·Hiroki ShudoKenichiro Itami
Oct 28, 2019·Frontiers in Chemistry·Dapeng LuPingwu Du
Jun 24, 2020·Chemistry : a European Journal·Kwan Yin CheungKenichiro Itami
Nov 17, 2020·Chemical Communications : Chem Comm·Kosuke WatanabeKenichiro Itami
Nov 17, 2020·Organic & Biomolecular Chemistry·Wenbo Wang, Xiangfeng Shao
Sep 23, 2020·Chemistry : a European Journal·Kiran Sagar UnikelaGraham J Bodwell
Oct 14, 2020·Angewandte Chemie·Yi HanChunyan Chi
Dec 30, 2020·Chemistry : a European Journal·Divanshu GuptaHolger F Bettinger
Jan 27, 2021·Nature Chemistry·Kwan Yin CheungKenichiro Itami
Jan 8, 2021·The Journal of Organic Chemistry·Yirui CaoLei Fang
Jan 12, 2021·Angewandte Chemie·Ke LiZhe Sun
Mar 3, 2021·Nature Chemistry·Birgit Esser, Mathias Hermann
Mar 19, 2021·Journal of the American Chemical Society·Steven StevensonHarry C Dorn
Feb 19, 2021·Angewandte Chemie·Zeming XiaQian Miao
Sep 10, 2020·Angewandte Chemie·Mathias HermannBirgit Esser
Apr 17, 2021·Nature Chemistry·Qing-Hui GuoJ Fraser Stoddart
Mar 30, 2021·Chemistry : a European Journal·Saber MirzaeiRaúl Hernández Sánchez
Jun 5, 2021·Journal of the American Chemical Society·Harrison M BergmanT Don Tilley
Jun 15, 2021·Chemical Science·Saber MirzaeiRaúl Hernández Sánchez
Aug 17, 2019·Journal of the American Chemical Society·Shuhei NishigakiKen Tanaka
Mar 16, 2019·Organic Letters·Songlin XueHiroko Yamada
Mar 25, 2019·Journal of the American Chemical Society·Xuefeng LuJishan Wu
Oct 23, 2018·Organic Letters·Nirob K SahaBradley L Merner
Sep 14, 2019·Accounts of Chemical Research·Yasutomo SegawaKenichiro Itami
Jul 30, 2019·The Journal of Organic Chemistry·Shuangjiang Li, Kung K Wang
Jul 1, 2020·Journal of the American Chemical Society·Yuanming LiKenichiro Itami
Dec 18, 2020·Organic Letters·Edison CastroRaúl Hernández Sánchez
Sep 23, 2021·Journal of the American Chemical Society·Wei FanJishan Wu

❮ 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.