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2 cooperative function with acid or base sites tal multi-metal interaction step site Ligand steric control electronic control electron transfer
3 Biomass onversion to hemicals by upported tal atalysts
4 cooperative function with acid or base sites tal multi-metal interaction step site Ligand steric control electronic control electron transfer
5 H H H H
6 cooperative function with acid or base sites tal multi-metal interaction step site Ligand steric control electronic control electron transfer
7 8 F 6 F Rh Rh LB film on glass Au l Ru l Au l Ru l Au Au thiolate monolayer on Au h 2 h 3 i() 2 h 2 h 3 i() 2 monolayer on 2 H 2 H 2 25 H T 60,000 (48 h) D. Milstein et al. cience 1997, 278, H 2 l 2 25 W. Tremel et al. Angew. hem. Int. Ed. 1998, 37, n h h TF 75,000 h -1 TF 1,700 h -1 A. Kakkar hem. Mater. 1999, 11, 269. h h
8 Diels-Alder M. Tada, Y. Iwasawa et al. J. atal. 2007, 245, 173. ee.. faltz et al. J. Am. hem. oc. 2005, 127, 820.
9 H H H ( ) 5 H 2 Ac Ac d H 3 H Ac Ac d H 3 ( ) 4 + H RhLn ( ) 5 2 hh RhLn RhLn 2 h Au atalyst hip on licon Wafer K. Hara et al. hem. ommun. 2007, atalyst hip on Gold urface K. Hara et al. Angew. hem. Int. Ed. 47, 2008, 5627.
10 Rh- H Au 1.0 mm EtH 25, 18 h Au [Rhl( 2 H 4 ) 2 ] 2 (5.0 mm) 6 H 6, min Au RhlLn RhlLn X, XAF Rh IR-RA() V() 0.69 nmol/cm 2 /Au = 0.30 I-M Rh0.69 nmol/cm 2 side view top view /Au = 0.33
![2 [Rhl( 2 H 4 ) 2 ] 2 5 x 5 mm 2 Au (Rh : = 1 : 1) (in H 2 l 2 ) Au Au + / = 75](/docs-images/100/146909543/images/11-1.jpg "000 (%) 80 60 000 / = 43 000 9 3 900 / = 43 000 36 0 3 15 000 Angew. hem. Int.")
11 EtH + 2 hh catalyst Hexane Eth 2 + H 2 (1.2 eq) (12 μmol) (0.12 ml) 25, 16 h RhlLn RhlLn [Rhl( 2 H 4 ) 2 ] 2 + catalyst h [Rhl( 2 H 4 ) 2 ] 2 [Rhl( 2 H 4 ) 2 ] 2 5 x 5 mm 2 Au (Rh : = 1 : 1) (in H 2 l 2 ) Au Au + / = (%) / = / = Angew. hem. Int. Ed. 47, 2008, 5627.
12 catalyst catalyst EtH + 2 hh Eth 2 + H 2 Hexane (1.2 eq) (12 μmol) (0.12 ml) 25, 16 h RhlLn RhlLn 1st use 1st recycle 2nd recycle 3rd recycle [Rhl( 2 H 4 ) 2 ] 2 + h (Rh : = 1 : 1) [Rhl( 2 H 4 ) 2 ] 2 Au 5 x 5 mm 2 (in H 2 l 2 ) Angew. hem. Int. Ed. 47, 2008, 5627.
13 H ( ) 5 (1.0 eq) catalyst + 2 hh + hexane ( ) H 4 25, 16 h (1.0 eq) H 2 (1.0 eq) ( ) 5 ( ) h 2 h catalyst RhlLn RhlLn [Rhl( 2 H 4 ) 2 ] 2 + h LnlRh LnlRh h h h h (Rh : = 1 : 1) (in H 2 l 2 ) Au (%) (%) Au > Angew. hem. Int. Ed. 47, 2008, 5627.
14 + Au surface EtH 25, 18 h [Rhl( 2 H 4 ) 2 ] 2 (5.0 mm) benzene 25, 15 min RhlL n H H (1.0 mm) + Au surface EtH 25, 18 h [Rhl( 2 H 4 ) 2 ] 2 (5.0 mm) benzene 25, 15 min RhlL n H H
15 H ( ) 2 h 5 [Au]-MA-Rh / n ( ) 5 (1.0 eq) (n = 10 or 16) hh + + hexane H 2 h ( ) 25, 16 h ( ) 4 4 (1.0 eq) H 2 (1.0 eq) n = 10 ( 10 H 21 H) n = 16 ( 16 H 33 H) 1 (%) n = 16 n = n% n% 0 RhlL n [Au]-MA-Rh / n (n = 10 or 16)
16 ompetitive Reaction between 1vs 2Alcohls ( ) 5 (1.0 eq) + H + 2 hh catalyst hexane 25, 16 h ( ) H 4 (1.0 eq) H 2 (1.0 eq) ( ) 5 ( ) h 2 h catalyst RhlLn RhlLn X u Au DTBM-Xantphos-u atalyst Tunover umber 1 selectivity (%) 58,000 >
17 cooperative function with acid or base sites tal multi-metal interaction step site Ligand steric control electronic control electron transfer
18 Thiol to Isocyanide RhLn RhLn RhLn Rhl() 2 Rhl() 2 Rhl() 2 Au Au tal-hosphine Terminated Thiolate tal- Diisocyanide
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21 X and I-M Analyses of tal Diisocyanide Monolayer Intensity (a.u.) 1s Rh 3d 5/2 l 2p Binding energy (ev) About 50% complexation between Rh and Intensity (a.u.) : Rh : l = 2.0 : 0.6 : 0.8 Binding energy (ev) The longer linker molecule, the more ordered structure. Rh density (I-M) 0.36 nmol/cm 2 ( cm -2 ) Rh density (I-M) 0.40 nmol/cm 2 ( cm -2 ) Density of isocyanide: About 0.7 nmol/cm 2 ( cm -2 ) : Rh : l = 2.0 : 0.8 : 1.2 Rhl(cod) Rhl(cod) Au Au Rhl(cod) Rhl(cod)
![Rh omplexiation with [Rhl(cod)] 2 Rhl(cod) Rhl(cod) top view Au Rhl(cod) Rhl(cod) side view](/docs-images/100/146909543/images/22-0.jpg "About 50% complexation between Rh and Density of isocyanide: About 0.")
22 Rh omplexiation with [Rhl(cod)] 2 Rhl(cod) Rhl(cod) top view Au Rhl(cod) Rhl(cod) side view About 50% complexation between Rh and Density of isocyanide: About 0.7 nmol/cm 2 ( cm -2 ) Au
![Rh omplexiation with [Rhl() 2 ] 2 Rh density (I-M) 0.](/docs-images/100/146909543/images/23-0.jpg "66 nmol/cm 2 (4.0 10 11 cm -2 ) top view : Rh : l = 2.0 : 1.")
23 Rh omplexiation with [Rhl() 2 ] 2 Rh density (I-M) 0.66 nmol/cm 2 ( cm -2 ) top view : Rh : l = 2.0 : 1.3 : 1.6 Rhl() 2 Rhl() 2 Rhl() 2 side view About 100% complexation between Rh and Density of isocyanide: About 0.7 nmol/cm 2 ( cm -2 ) Au
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25
26 1,4-Hydrogenation of,-arbonyl ompounds enone / Rh = 72,000 Rhl() 2 Rhl() 2 Rhl() 2 atalyst [Rhl() 2 ] Au Time (h) onversion (%) electivity (%) (c-hexanone) 26
27 1,4-Hydrogenation of,-arbonyl ompounds onversion (%) electivity (%) Rhl() 2 Rhl() 2 Rhl() H H H h h 2 H 5 h Au
28 tal multi-metal interaction cooperative function with acid or base sites step site Ligand steric control electronic control electron transfer Homogeneous atalyst Designability Diversity Heterogeneous atalyst eparation, Recovery tability Mixed-Monolayer atalyst Monolayer atalyst
29 Addition of sp 3 -H Bond to Alkyne with u-diisocyanide Monolayer on Au urface h + H 40, 24 h h H (solvent) under 2 T (per u) = 1,000 25,000 u u u o conversion with ui, u(ac) 2 cf. Y. Zhang et al. ynthesis, 2009, ubr (10 mol%) TBH (1-1.2 equiv.) Au u = ui, u(ac) 2
30 Reaction rofile u u romoted by catalyst
31 roposed chanism
32 roposed chanism TBH TBH (R = t Bu, t Bu, H)
33
34 cooperative function with acid or base sites tal multi-metal interaction step site Ligand steric control electronic control electron transfer
35 rof. Masaya awamura ollaboration rof. Kohei Uosaki Dr. Toshihiro Kondo Dr. atoru Takakusagi XAF ollaborators & Acknowledgment Dr. Takuya Masuda rof. Kiyotaka Asakura rof. W. J. hun X rof. Katsuaki himazu Dr. YusukeYoshinaga rof. W. J. hun Dr. Ryuto Akiyama Ms. Yuriko Ishiguro
36 ollaborators & Acknowledgment rof. Atsushi Fukuoka Dr. achin Jagtap Au urface rof. Kohei Uosaki Dr. Hidenori oguchi rof. Katsuaki himazu Dr. Toshikazu Kawaguchi Mr. Yoshinori Mr. Kotaro amba KEK rof. Kiyotaka Asakura rof. W. J. hun HREEL rof. Maki Kawai Dr. Hiroyuki Kato
37 H H H H
38 H H H H H MM m 2 /g m 2 /g 4 nm nm
39 H H H H H 1) Tf 2) Hl, EtH H H H H H H H H H H as-synthesized MM-41
40 H TM-MM H H H or H H H H H H H H H u(ac) 2 H 2 (5 wt% u) H K, 22 h 1) filtration 2) wash with toluene 3) drying under vacuum u/tm-mm (0.8 wt% u) u/mm (1.1 wt% u) MM-41 H H H 40
41 H 0.3 mmol DM (2,6-dimethylphenol) atm u/tm-mm or u/mm (/ = 50) pyridine (0.1 ml) toluene (0.5 ml) 298 K E J.. Kondo et al., Macromolecules, 37, 9657 (2004) J.. Kondo et al, hem. Lett. 34, 662 (2005) H n H G : MR : G :
42 2500 u/tm-mm Average molecular weight (Mn) u/mm : u/tm-mm > u/mm u/tm-mm > u/mm reaction time/h
43 m + m u u u u u u u/tm-mm u/mm
44 , U.. DE Ames Laboratory Department of hemistry, Iowa tate University Dr. Jerzy W. Wiench rof. Marek ruski rof. Victor.-Y. Lin KEK (and ring-8) rof. W. J. hun (IU)
45 eriodic soporous rganosilica (M) soporous lica ore size2~50 nm. High specific surface area. Amorphous. In addition to their characteristics rganic soporous lica R R rystal-like wall structure. Direct Functionalization in framework. tructure regularity.
46
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![revious Works of Artificial hotosynthesis with 2 and H 2 2 h H 2 Toyota, 2011 Ti 2 e H + 2 H h [Ru(4,4 -diphosphate ethyl- 2,2 -bipyridine)() 2 l 2 ]/In. ato et al., J. Am. hem. oc.](/docs-images/100/146909543/images/48-0.jpg ", 133, 15240 (2011). The efficiency : 0.04% 2 h H 2 anasonic, 2012 itride emiconductor e H + tal atalyst The efficiency : 0.2% 2 HH h Efficiencies are very low. Electrodes are necessary.")
48 revious Works of Artificial hotosynthesis with 2 and H 2 2 h H 2 Toyota, 2011 Ti 2 e H + 2 H h [Ru(4,4 -diphosphate ethyl- 2,2 -bipyridine)() 2 l 2 ]/In. ato et al., J. Am. hem. oc., 133, (2011). The efficiency : 0.04% 2 h H 2 anasonic, 2012 itride emiconductor e H + tal atalyst The efficiency : 0.2% 2 HH h Efficiencies are very low. Electrodes are necessary. M catalyst Quantum yield : 1.2%.
49 h
50 H H H H
51
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