Triangulene

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{{wiktionary}}

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'''Triangulene''' (also known as Clar's hydrocarbon) is the smallest [[Triplet state|triplet-ground-state]] [[Polycyclic aromatic hydrocarbon|polybenzenoid]].{{GoldBookRef |title=biradical |file=B00671 }} It exists as a [[biradical]] with the chemical formula {{chem|C|22|H|12}}.{{Cite web|url=http://www.chemspider.com/Chemical-Structure.58825768.html|title=triangulene {{!}} C22H12 {{!}} ChemSpider|website=www.chemspider.com|access-date=2017-02-19}} It was first hypothesized by [[Czech Republic|Czech]] chemist [[Erich Clar]] in 1953.{{cite journal |last1=Ball |first1=Philip |title=Elusive triangulene created by moving atoms one at a time |journal=Nature |date=February 2017 |volume=542 |issue=7641 |pages=284–285 |doi=10.1038/nature.2017.21462 |pmid=28202993 |bibcode=2017Natur.542..284B |s2cid=4398214 |doi-access=free }} Its first confirmed synthesis was published in a February 2017 issue of ''[[Nature Nanotechnology]]'', in a project led by researchers David Fox and Anish Mistry at the [[University of Warwick]] in collaboration with [[IBM]].{{cite journal |last1=Pavliček |first1=Niko |last2=Mistry |first2=Anish |last3=Majzik |first3=Zsolt |last4=Moll |first4=Nikolaj |last5=Meyer |first5=Gerhard |last6=Fox |first6=David J. |last7=Gross |first7=Leo |title=Synthesis and characterization of triangulene |journal=Nature Nanotechnology |date=April 2017 |volume=12 |issue=4 |pages=308–311 |doi=10.1038/nnano.2016.305 |pmid=28192389 |bibcode=2017NatNa..12..308P |url=http://wrap.warwick.ac.uk/86722/1/WRAP_ch-030317-wrap_-cusersdavid_foxdesktop40triangulene_complete_accepted.pdf }} Other attempts by [[Japan]]ese researchers have been successful only in making substituted triangulene derivatives.{{Cite journal|last1=Morita|first1=Yasushi|last2=Suzuki|first2=Shuichi|last3=Sato|first3=Kazunobu|last4=Takui|first4=Takeji|title=Synthetic organic spin chemistry for structurally well-defined open-shell graphene fragments|journal=Nature Chemistry|volume=3|issue=3|pages=197–204|doi=10.1038/nchem.985|pmid=21336324|year=2011|bibcode=2011NatCh...3..197M}}

'''Triangulene''' (also known as Clar's hydrocarbon) is the smallest [[Triplet state|triplet-ground-state]] [[Polycyclic aromatic hydrocarbon|polybenzenoid]].{{GoldBookRef |title=biradical |file=B00671 }} It exists as a [[biradical]] with the chemical formula {{chem|C|22|H|12}}.{{Cite web|url=http://www.chemspider.com/Chemical-Structure.58825768.html|title=triangulene {{!}} C22H12 {{!}} ChemSpider|website=www.chemspider.com|access-date=2017-02-19}} It was first hypothesized by [[Czech Republic|Czech]] chemist [[Erich Clar]] in 1953.{{cite journal |last1=Ball |first1=Philip |title=Elusive triangulene created by moving atoms one at a time |journal=Nature |date=February 2017 |volume=542 |issue=7641 |pages=284–285 |doi=10.1038/nature.2017.21462 |pmid=28202993 |bibcode=2017Natur.542..284B |s2cid=4398214 |doi-access=free }} Its first confirmed synthesis was published in a February 2017 issue of ''[[Nature Nanotechnology]]'', in a project led by researchers David Fox and Anish Mistry at the [[University of Warwick]] in collaboration with [[IBM]].{{cite journal |last1=Pavliček |first1=Niko |last2=Mistry |first2=Anish |last3=Majzik |first3=Zsolt |last4=Moll |first4=Nikolaj |last5=Meyer |first5=Gerhard |last6=Fox |first6=David J. |last7=Gross |first7=Leo |title=Synthesis and characterization of triangulene |journal=Nature Nanotechnology |date=April 2017 |volume=12 |issue=4 |pages=308–311 |doi=10.1038/nnano.2016.305 |pmid=28192389 |bibcode=2017NatNa..12..308P |url=http://wrap.warwick.ac.uk/86722/1/WRAP_ch-030317-wrap_-cusersdavid_foxdesktop40triangulene_complete_accepted.pdf }} Other attempts by [[Japan]]ese researchers including Yasushi Morita and Takeji Takui have been successful only in making substituted triangulene derivatives.{{Cite journal|last1=Morita|first1=Yasushi|last2=Suzuki|first2=Shuichi|last3=Sato|first3=Kazunobu|last4=Takui|first4=Takeji|title=Synthetic organic spin chemistry for structurally well-defined open-shell graphene fragments|journal=Nature Chemistry|volume=3|issue=3|pages=197–204|doi=10.1038/nchem.985|pmid=21336324|year=2011|bibcode=2011NatCh...3..197M}}

A six-step synthesis yielded two isomers of dihydrotriangulene which were then deposited on [[xenon]] or [[copper]] base. The researchers used a combined [[Scanning tunneling microscope|scanning tunneling]] and [[Atomic-force microscopy|atomic force]] microscope (STM/AFM) to remove individual [[hydrogen]] atoms. The synthesized molecule of triangulene remained stable at high-[[vacuum]] low-[[Cryogenics|temperature]] conditions for four days, giving the scientists plenty of time to characterize it (also using STM/AFM).

A six-step synthesis yielded two isomers of dihydrotriangulene which were then deposited on [[xenon]] or [[copper]] base. The researchers used a combined [[Scanning tunneling microscope|scanning tunneling]] and [[Atomic-force microscopy|atomic force]] microscope (STM/AFM) to remove individual [[hydrogen]] atoms. The synthesized molecule of triangulene remained stable at high-[[vacuum]] low-[[Cryogenics|temperature]] conditions for four days, giving the scientists plenty of time to characterize it (also using STM/AFM).