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- 저자 : Tsurumaki, Eiji (검색결과 2 건)
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Subporphyrinato Boron(III) Hydrides
Tsurumaki, Eiji,Sung, Jooyoung,Kim, Dongho,Osuka, Atsuhiro American Chemical Society 2015 JOURNAL OF THE AMERICAN CHEMICAL SOCIETY - Vol.137 No.3
<P>Subporphyrinato boron(III) hydrides were prepared by reduction of subporphyrinato boron(III) methoxides with diisobutylaluminum hydride (DIBAL-H) in good yields. The authenticity of the B–H bond has been unambiguously confirmed by a <SUP>1</SUP>H NMR signal that appears as a broad quartet at −2.27 ppm with a large coupling constant with the central <SUP>11</SUP>B, characteristic B–H infrared stretching frequencies, and single crystal X-ray diffraction analysis. Red shifts in the corresponding absorption and fluorescence profiles are accounted for in terms of the electron-donating nature of the B-hydride. The hydridic character of subporphyrinato boron(III) hydrides has been demonstrated by the production of H<SUB>2</SUB> via reaction with water or HCl, and controlled reductions of aromatic aldehydes and imines in the presence of a catalytic amount of Ph<SUB>3</SUB>C[B(C<SUB>6</SUB>F<SUB>5</SUB>)<SUB>4</SUB>].</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/jacsat/2015/jacsat.2015.137.issue-3/ja5126269/production/images/medium/ja-2014-126269_0009.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ja5126269'>ACS Electronic Supporting Info</A></P>
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Tsurumaki, Eiji,Inokuma, Yasuhide,Easwaramoorthi, Shanmugam,Lim, Jong Min,Kim, Dongho,Osuka, Atsuhiro WILEY-VCH Verlag 2009 Chemistry Vol.15 No.1
<P>Effective peripheral fabrication methods of meso-aryl-substituted subporphyrins were explored for the first time. Hexabrominated subporphyrins 2 were prepared quantitatively from the bromination of subporphyrins 1 with bromine. Hexaphenylated subporphyrins 3 and hexaethynylated subporphyrins 4 and 5 were synthesized by Suzuki–Miyaura coupling and Stille coupling, respectively, in good yields. X-ray crystal structures of 2 b, 3 b, 4 b, and 5 a revealed preservation of the bowl-shaped bent structures with bowl depths similar to that of 1. Hexaethynylated subporphyrins exhibit large two-photon-absorption cross-sections due to effective delocalization of the conjugated network to the ethynyl substituents.</P> <B>Graphic Abstract</B> <P>β-Substituted subporphyrins: β-Hexabrominated, hexaphenylated, and hexaethynylated (see picture) meso-aryl subporphyrins are reported as the first products of β-peripherally fabricated subporphyrins. X-ray diffraction analysis revealed that all hexasubstituted subporphyrins preserve bowl-shaped structures. Detailed NMR, electrochemical, optical, and theoretical studies were carried out. <img src='wiley_img/09476539-2009-15-1-CHEM200801802-content.gif' alt='wiley_img/09476539-2009-15-1-CHEM200801802-content'> </P>
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