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Aratani, Naoki,Kim, Dongho,Osuka, Atsuhiro Wiley (John WileySons) 2009 Chemistry, an Asian journal Vol.4 No.8
<P>Recent progress in the synthesis of covalently linked porphyrin arrays with large two-Photon absorption (TPA) cross-section values has been reviewed with a particular focus on the relation of TPA properties with molecular structures. Covalently linked porphyrin arrays continue to be important and useful for the creation of functional materials owing to their chemical robustness, fine-tuning, and easy manipulation. More importantly, the porphyrin electronic systems are quite susceptible to periphery conjugative perturbations, hence allowing facile fabrications to extensively delocalized systems. This property has been used for exploration of porphyrin-based molecular systems with large TPA values, demonstrating a general trend that enhancement in electronic interactions leads to large TPA cross-section values. As a representative example, the porphyrin tapes exhibit larger TPA values owing to the fully delocalized nature of the pi-electrons. This Focus Review will help understand the structural requirements of porphyrin arrays with large TPA values, which will be useful for future applications in optical communication in the IR region.</P>
Directly Pd(II)-Bridged Porphyrin Belts with Remarkable Curvatures
Song, Jianxin,Aratani, Naoki,Heo, Ji Haeng,Kim, Dongho,Shinokubo, Hiroshi,Osuka, Atsuhiro American Chemical Society 2010 JOURNAL OF THE AMERICAN CHEMICAL SOCIETY - Vol.132 No.34
<P>A β,β′-doubly 2,6-pyridylene-bridged porphyrin dimer and trimer were prepared by Suzuki−Miyaura coupling reactions and confirmed to have largely bent structures. These oligoporphyrins were readily metalated via <I>meso</I>-C−H bond activation with the assistance of the pyridyl nitrogen atoms to produce the corresponding Pd(II) complexes, which display even larger bent structures and larger TPA values at 800 nm.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jacsat/2010/jacsat.2010.132.issue-34/ja1046654/production/images/medium/ja-2010-046654_0004.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ja1046654'>ACS Electronic Supporting Info</A></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ja1046654'>ACS Electronic Supporting Info</A></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ja1046654'>ACS Electronic Supporting Info</A></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ja1046654'>ACS Electronic Supporting Info</A></P>
Rath, Harapriya,Aratani, Naoki,Lim, Jong Min,Lee, Jae Seok,Kim, Dongho,Shinokubo, Hiroshi,Osuka, Atsuhiro Royal Society of Chemistry 2009 Chemical communications Vol.2009 No.25
<P>Metalation of [28]hexaphyrin(1.1.1.1.1.1) with [RhCl(CO)<SUB>2</SUB>]<SUB>2</SUB> resulted in the formation of an antiaromatic bis-Rh(<SMALL>I</SMALL>) complex, which can be oxidized to an aromatic bis-Rh(<SMALL>I</SMALL>) complex with retention of its rectangular structure.</P> <P>Graphic Abstract</P><P>Metalation of [28]hexaphyrin(1.1.1.1.1.1) with [RhCl(CO)<SUB>2</SUB>]<SUB>2</SUB> resulted in the formation of an antiaromatic bis-Rh(<SMALL>I</SMALL>) complex. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=b905859a'> </P>
Porphyrin–hexaphyrin hybrid tapes
Tanaka, Takayuki,Aratani, Naoki,Lim, Jong Min,Kim, Kil Suk,Kim, Dongho,Osuka, Atsuhiro Royal Society of Chemistry 2011 Chemical science Vol.2 No.7
<P>A <I>meso-meso</I> linked porphyrin–hexaphyrin hybrid was synthesized by the cross condensation using <I>meso</I>-porphyrinyl-dipyrromethane and was oxidized with DDQ-Sc(OTf)<SUB>3</SUB> to afford a porphyrin–[26]hexaphyrin hybrid tape that was reduced with NaBH<SUB>4</SUB> to give a porphyrin–[28]hexaphyrin hybrid tape. Fully electronic conjugations in the hybrid tapes are observed in the UV/vis/NIR absorption spectra, electrochemistry, and excited-state dynamics.</P> <P>Graphic Abstract</P><P>A <I>meso-meso</I> linked porphyrin–hexaphyrin hybrid was synthesized by the cross condensation reaction and was oxidized with DDQ-Sc(OTf)<SUB>3</SUB> to afford a porphyrin–[26]hexaphyrin hybrid tape that can be reduced to [28]hexaphyrin congener. Fully electronic conjugations in the hybrid tapes are observed in the UV/vis/NIR absorption spectra, electrochemistry, and excited-state dynamics. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c1sc00228g'> </P>
Porphyrin “Lego Block” Strategy To Construct Directly meso–β Doubly Linked Porphyrin Rings
Song, Jianxin,Aratani, Naoki,Kim, Pyosang,Kim, Dongho,Shinokubo, Hiroshi,Osuka, Atsuhiro WILEY-VCH Verlag 2010 Angewandte Chemie Vol.122 No.21
<B>Graphic Abstract</B> <P>Eingerastet: Die Suzuki-Miyaura-Kupplung von β,β′-diborylierten mit meso,meso′-dibromierten Porphyrinblöcken wird für den Aufbau direkt doppelt meso-β-verknüpfter Porphyrinringe genutzt, darunter zweier Tetraporphyrinringe, Hexaporphyrinringe und eines verbrückten Heptaporphyrins (siehe Bild). <img src='wiley_img_2010/00448249-2010-122-21-ANGE201000915-content.gif' alt='wiley_img_2010/00448249-2010-122-21-ANGE201000915-content'> </P>
Yang, Jaesung,Yoo, Hyejin,Aratani, Naoki,Osuka, Atsuhiro,Kim, Dongho WILEY-VCH Verlag 2009 Angewandte Chemie. international edition Vol.48 No.24
<P>Down to the wire: Photobleaching dynamics show the exciton delocalization length of directly linked porphyrin arrays (see picture) to be about four or five porphyrin units at the single-molecule level. This result provides a better understanding of how light-signal transmission occurs in the solid state and gives a perspective for the porphyrin arrays to be used as single-molecule photonic wires. <img src='wiley_img/14337851-2009-48-24-ANIE200901375-content.gif' alt='wiley_img/14337851-2009-48-24-ANIE200901375-content'> </P> <B>Graphic Abstract</B> <P>Down to the wire: Photobleaching dynamics show the exciton delocalization length of directly linked porphyrin arrays (see picture) to be about four or five porphyrin units at the single-molecule level. This result provides a better understanding of how light-signal transmission occurs in the solid state and gives a perspective for the porphyrin arrays to be used as single-molecule photonic wires. <img src='wiley_img/14337851-2009-48-24-ANIE200901375-content.gif' alt='wiley_img/14337851-2009-48-24-ANIE200901375-content'> </P>
Strategic Synthesis of 2,6-Pyridylene-Bridged β-to-β Porphyrin Nanorings through Cross-Coupling
Song, Jianxin,Kim, Pyosang,Aratani, Naoki,Kim, Dongho,Shinokubo, Hiroshi,Osuka, Atsuhiro WILEY-VCH Verlag 2010 Chemistry Vol.16 No.10
<B>Graphic Abstract</B> <P>The bridge determines the size of the loop? Palladium-catalyzed cross-coupling of borylporphyrins led to the construction of β-pyridine-bridged porphyrin nanorings in good yields (around 55–60 %; see scheme). The photophysical study revealed that these nanorings exhibit weakly coupled chromophores and longer fluorescent lifetimes, which is an apparent advantage in the process of efficient excited energy transfer. <img src='wiley_img_2010/09476539-2010-16-10-CHEM200903177-content.gif' alt='wiley_img_2010/09476539-2010-16-10-CHEM200903177-content'> </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>