TY - JOUR
T1 - Bottom-up synthesis of finite models of helical (n,m)-single-wall carbon nanotubes
AU - Hitosugi, Shunpei
AU - Nakanishi, Waka
AU - Yamasaki, Takashi
AU - Isobe, Hiroyuki
N1 - Funding Information:
This study was partly supported by KAKENHI (21685005, 20108015, 22550094) and the Research Seeds Quest Program (JST). We thank Professor T. Imamoto (Chiba University) for the generous gift of chiral ligands, Professor N. Teramae (Tohoku University) for the CD instrument, Professor H. Tokuyama (Tohoku University) for the NMR instrument, Professor T. Iwamoto (Tohoku University) for the X-ray instrument, JEOL for the DART MS instruments, Nacalai Tesque for the first sample of cholester columns and Central Glass Company for the gift of hexafluoroisopropanol. S.H. thanks the Global COE program (Molecular Complex Chemistry) for the predoctoral fellowship.
PY - 2011
Y1 - 2011
N2 - The bottom-up synthesis of hoop-shaped aromatic hydrocarbons is currently attracting interest, because they can serve as finite models of single-wall carbon nanotubes (SWNTs). Models for chiral (n,m)-SWNTs, particularly those with optical activity, have not been synthesized but are of special interest owing to their anomalous helical network of sp 2 -carbons. Here we show that finite model compounds for (12,8)-, (11,9)- and (10,10)-SWNTs are synthetically accessible by a stepwise macrocyclization of [4]phenacene, a compound that bears fused benzene rings in a zigzag arrangement, and we can isolate and identify all the isomers including the enantiomers with (P)- and (M)-helicity. The complete isolation and identification of the model compounds led to the first examination of the stereo-disproportionation of chiral SWNT models, which encourages the future studies on asymmetric induction for the synthesis.
AB - The bottom-up synthesis of hoop-shaped aromatic hydrocarbons is currently attracting interest, because they can serve as finite models of single-wall carbon nanotubes (SWNTs). Models for chiral (n,m)-SWNTs, particularly those with optical activity, have not been synthesized but are of special interest owing to their anomalous helical network of sp 2 -carbons. Here we show that finite model compounds for (12,8)-, (11,9)- and (10,10)-SWNTs are synthetically accessible by a stepwise macrocyclization of [4]phenacene, a compound that bears fused benzene rings in a zigzag arrangement, and we can isolate and identify all the isomers including the enantiomers with (P)- and (M)-helicity. The complete isolation and identification of the model compounds led to the first examination of the stereo-disproportionation of chiral SWNT models, which encourages the future studies on asymmetric induction for the synthesis.
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U2 - 10.1038/ncomms1505
DO - 10.1038/ncomms1505
M3 - Article
AN - SCOPUS:80055038211
VL - 2
JO - Nature Communications
JF - Nature Communications
SN - 2041-1723
IS - 1
M1 - 492
ER -