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Naoda, Koji,Mori, Hirotaka,Oh, Juwon,Park, Kyu Hyung,Kim, Dongho,Osuka, Atsuhiro American Chemical Society 2015 Journal of organic chemistry Vol.80 No.23
<P>5,20-Di(pyridin-2-yl)-[28]hexaphyrin(1.1.1.1.1.1) 7 was prepared and characterized as a stable Huckel antiaromatic molecule with a dumbbell-like structure stabilized by effective intramolecular hydrogen bonding interactions involving the 2-pyridyl nitrogen atoms. Pd(II) metalation of 7 afforded two bis-Pd(II) complexes, 9-syn and 9-anti, whose structures are rigidly held by Pd(II) coordination, rendering 9-syn to be nonaromatic because of its highly distorted structure and 9-anti to be Huckel antiaromatic because of its enforced planar dumbbell structure. In contrast, protonation of 7 with methanesulfonic acid (MSA) led to the formation of its triprotonated species 7H(3), which has been shown to take on twisted conformations with Mobius aromaticity in CH2Cl2, while the structure was held to be a planar rectangular conformation in the crystal. Excited-state dynamics were measured for 7, 7H(3), 9-syn, and 9-anti, which indicated their electronic nature to be antiaromatic, aromatic, nonaromatic, and antiaromatic, respectively.</P>
Innentitelbild: Hexaphyrin Fused to Two Anthracenes (Angew. Chem. 39/2012)
Naoda, Koji,Mori, Hirotaka,Aratani, Naoki,Lee, Byung Sun,Kim, Dongho,Osuka, Atsuhiro WILEY‐VCH Verlag 2012 Angewandte Chemie Vol.124 No.39
<P><I>π</I>‐expandierte Porphyrinoide in denen aromatische Strukturteile an den Porphyrinring kondensiert sind, rücken zunehmend in den Blickpunkt. In ihrer Zuschrift auf S. 9994 ff. berichten D. Kim, A. Osuka et al. über die Bildung eines Hexaphyrins, das mit zwei Anthracenylsubstituenten oxidativ kondensiert wurde. Das rechteckige konjugierte System verleiht dem kondensierten Hexaphyrin eine bemerkenswerte rotverschobene und eine ungewöhnlich scharfe Q‐Banden‐ähnliche Absorption bei 1467nm. (Photos: kyoto‐design.jp)</P>
Sung, Young Mo,Yoon, Min-Chul,Lim, Jong Min,Rath, Harapriya,Naoda, Koji,Osuka, Atsuhiro,Kim, Dongho Nature Publishing Group, a division of Macmillan P 2015 Nature chemistry Vol.7 No.5
The reversal of (anti)aromaticity in a molecule's triplet excited state compared with its closed-shell singlet ground state is known as Baird's rule and has attracted the interest of synthetic, physical organic chemists and theorists because of the potential to modulate the fundamental properties of highly conjugated molecules. Here we show that two closely related bis-rhodium hexaphyrins (R26H and R28H) containing [26] and [28] π-electron peripheries, respectively, exhibit properties consistent with Baird's rule. In the ground state, R26H exhibits a sharp Soret-like band and distinct Q-like bands characteristic of an aromatic porphyrinoid, whereas R28H exhibits a broad absorption spectrum without Q-like bands, which is typical of an antiaromatic porphyrinoid. In contrast, the T–T absorption of R26H is broad, weak and featureless, whereas that of R28H displays an intense and sharp Soret-like band. These spectral signatures, in combination with quantum chemical calculations, are in line with qualitative expectations based on Baird's rule.