TY - JOUR
T1 - Conformational Fixation of a Rectangular Antiaromatic [28]Hexaphyrin Using Rationally Installed Peripheral Straps
AU - Yoneda, Tomoki
AU - Kim, Taeyeon
AU - Soya, Takanori
AU - Neya, Saburo
AU - Oh, Juwon
AU - Kim, Dongho
AU - Osuka, Atsuhiro
N1 - Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2016/3/18
Y1 - 2016/3/18
N2 - A rectangular [28]hexaphyrin bearing outer straps at the long side has been synthesized by SNAr reaction of [26]hexaphyrin with allyl alcohol, intramolecular olefin metathesis by using Hoveyda-Grubbs second-generation catalyst, and reduction with NaBH4. The peripheral straps enforce a rectangular conformation for the [28]hexaphyrin, which shows Hückel antiaromatic character, as confirmed by its planar X-ray structure, a strong paratropic ring current, characteristic UV/Vis/NIR absorption features, small electrochemical HOMO-LUMO gap, and very fast S1 decay.
AB - A rectangular [28]hexaphyrin bearing outer straps at the long side has been synthesized by SNAr reaction of [26]hexaphyrin with allyl alcohol, intramolecular olefin metathesis by using Hoveyda-Grubbs second-generation catalyst, and reduction with NaBH4. The peripheral straps enforce a rectangular conformation for the [28]hexaphyrin, which shows Hückel antiaromatic character, as confirmed by its planar X-ray structure, a strong paratropic ring current, characteristic UV/Vis/NIR absorption features, small electrochemical HOMO-LUMO gap, and very fast S1 decay.
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U2 - 10.1002/chem.201600262
DO - 10.1002/chem.201600262
M3 - Article
C2 - 26870921
AN - SCOPUS:84960812791
SN - 0947-6539
VL - 22
SP - 4413
EP - 4417
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 13
ER -