Abstract
Oxidative fusion reactions of ortho-phenylene-bridged cyclic hexapyrroles and hexathiophenes furnished novel closed helicenes in a selective manner. X-Ray diffraction analysis unambiguously revealed the structures to be a closed pentaaza[9]helicene, the longest azahelicene reported so far, and an unexpected double-helical structure of hexathia[9]/[5]helicene, whose formation was assumed to result from multiple oxidative fusion along with a 1,2-aryl shift. The pentaaza[9]helicene exhibited well-defined emission with high fluorescence quantum yield (ΦF=0.31) among the known [9]helicenes. Chiral resolution of the racemic pentaaza[9]helicene and hexathia[9]/[5]helicene were achieved by chiral-phase HPLC and the enantiomers were characterized by circular dichroism spectra and DFT calculations.
| Original language | English |
|---|---|
| Pages (from-to) | 14688-14693 |
| Number of pages | 6 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 56 |
| Issue number | 46 |
| DOIs | |
| Publication status | Published - 2017 Nov 13 |
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All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)
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Closed Pentaaza[9]helicene and Hexathia[9]/[5]helicene : Oxidative Fusion Reactions of ortho-Phenylene-Bridged Cyclic Hexapyrroles and Hexathiophenes. / Chen, Fengkun; Tanaka, Takayuki; Hong, Yong Seok; Mori, Tadashi; Kim, Dongho; Osuka, Atsuhiro.
In: Angewandte Chemie - International Edition, Vol. 56, No. 46, 13.11.2017, p. 14688-14693.Research output: Contribution to journal › Article
TY - JOUR
T1 - Closed Pentaaza[9]helicene and Hexathia[9]/[5]helicene
T2 - Oxidative Fusion Reactions of ortho-Phenylene-Bridged Cyclic Hexapyrroles and Hexathiophenes
AU - Chen, Fengkun
AU - Tanaka, Takayuki
AU - Hong, Yong Seok
AU - Mori, Tadashi
AU - Kim, Dongho
AU - Osuka, Atsuhiro
PY - 2017/11/13
Y1 - 2017/11/13
N2 - Oxidative fusion reactions of ortho-phenylene-bridged cyclic hexapyrroles and hexathiophenes furnished novel closed helicenes in a selective manner. X-Ray diffraction analysis unambiguously revealed the structures to be a closed pentaaza[9]helicene, the longest azahelicene reported so far, and an unexpected double-helical structure of hexathia[9]/[5]helicene, whose formation was assumed to result from multiple oxidative fusion along with a 1,2-aryl shift. The pentaaza[9]helicene exhibited well-defined emission with high fluorescence quantum yield (ΦF=0.31) among the known [9]helicenes. Chiral resolution of the racemic pentaaza[9]helicene and hexathia[9]/[5]helicene were achieved by chiral-phase HPLC and the enantiomers were characterized by circular dichroism spectra and DFT calculations.
AB - Oxidative fusion reactions of ortho-phenylene-bridged cyclic hexapyrroles and hexathiophenes furnished novel closed helicenes in a selective manner. X-Ray diffraction analysis unambiguously revealed the structures to be a closed pentaaza[9]helicene, the longest azahelicene reported so far, and an unexpected double-helical structure of hexathia[9]/[5]helicene, whose formation was assumed to result from multiple oxidative fusion along with a 1,2-aryl shift. The pentaaza[9]helicene exhibited well-defined emission with high fluorescence quantum yield (ΦF=0.31) among the known [9]helicenes. Chiral resolution of the racemic pentaaza[9]helicene and hexathia[9]/[5]helicene were achieved by chiral-phase HPLC and the enantiomers were characterized by circular dichroism spectra and DFT calculations.
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U2 - 10.1002/anie.201708429
DO - 10.1002/anie.201708429
M3 - Article
VL - 56
SP - 14688
EP - 14693
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 46
ER -