Expanded porphyrinoids via intramolacular oxidating coupling - synthesis and properties Duoduo Bao & Jan Lewtak

Conjugated Porphyrin Tapes Meso-meso singly linked arrays Meso-meso ß-ß ß-ß triply linked arrays Tsuda, A., Osuka, A., Adv. Mat, 2002, 14, %

Conjugated Porphyrin Tapes avoiding chlorination Up to 12, 61-90% Tsuda, A., Osuka, A., Adv. Mat, 2002, 14, Stability

Metal-Dependent Regioselective Oxidative Coupling Kamo, M., Osuka, A., Org. Lett., 2003, 5, Sc(OTf) 3 reacts with DDQ

Gold-Mediated Fusion Reaction of Porphyrin Dimer TPA values Osuka et al., Org Lett., 2006

Coming from Porphyrin-Ferrocene Dyad... Cammidge, A.N., Berber, G., Hughes, D.L., Org. Lett., 2005, 7, Absence of ferrocene

Meso- Doubly Linked Zn(II) Porphyrin Trimers Ordinary approach – only anti Ikeda, T., Aratani, N., Kim, D., Osuka, A., Org. Lett., 2009, 5,

Meso- Doubly Linked Zn(II) Porphyrin Trimers Ikeda, T., Aratani, N., Kim, D., Osuka, A., Org. Lett., 2009, 5, TPA 3<2

Pyrene-Fused Porphyrins: Yamane, O., Sugiura, K., Miyasaka, H., Yamashita, M., Chem Lett. 2004, 33, K/Na

A Quadruply Azulene-Fused Porphyrin 16% 12% Kim, K.K., Noh, S.B., Kim, D., Osuka, A., Angew. Chem, 2006, 45, %84%60% TPA cross section Values: 9 – 340 GM GM GM

Expanding the Porphyrin π-System by Fusion with Anthracene Anderson, H.L., Davis N.L.S., Pawlicki, M., Org. Lett., 2008, 10, 3945–3947

Bis-Anthracene Fused Porphyrins Anderson, H.L., Davis N.L.S., Thompson, A.L., Org. Lett., 2010, ASAP IR-A: 700 nm–1400 nm (0,7 µm – 1.4 µm) IR-B: 1400 nm–3000 nm (1.4 µm – 3 µm) IR-C: 3000 nm–1 mm (3 µm – 1000 µm)

П -elongated porphyrin for dye- sensitized cells Imahori, H., Matano, Y., Tanaka, M., Chem Comm., 2007, larger absorptivity low symmetry HOMO-LUMO gap

Oxidative Rearrangement of Dispiro-Porphodimethenes Harmjanz, M., Scott, M.J., Angew. Chem. Int. Ed., 2004, 43,

A Hexagonal Prismatic Porphyrin Array Yoon M., Yoon Z.S, Kim, D., Osuka, A., J. Phys. Chem., 2007, 111, Osuka et al.., Angew. Chem. Int. Ed, 2010, in press

Fused Tetrameric Porphyrin Sheet Nakamura, Y.,Aratani, N., Shinokubo,H., Takagi, A., Matsumoto, T., Osuka, A., J. Am. Chem. Soc. 2006, 128,

Intramolecular Pd(0) catalysed coupling on ortho-iodinated meso-phenyl porphyrins Boyle, R.W., Fox., S., Chem Comm., 2004, Matano, Y., Tanaka, M., Chem Lett., 2004, 37,

Summary Red shifted, broadened spectrum Increasing of TPA cross section value Nonlinear optical materials PDT Solar energy collecting

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