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- In relation to this article, we declare that there is no conflict of interest.
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Received July 12, 2003
Accepted October 9, 2003
- This is an Open-Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/bync/3.0) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
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Internal/External Use of Dendrimer in Catalysis
School of Chemical Engineering and Institute of Chemical Processes, Seoul National University, Kwanak-ku, Seoul 151-742, Korea
Korean Journal of Chemical Engineering, January 2004, 21(1), 81-97(17), 10.1007/BF02705384
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Abstract
Dendrimers, well-defined hyper-branched macromolecules with characteristic globular structures, have inspired chemists and chemical engineers to develop new materials and several applications have been explored. The dendritic molecule has emerged as an attractive material in the field of catalysis and various dendrimer catalysts have been applied not only to catalytic reactions but also to non-catalytic ones such as nanoscale reactor systems. This article_x000D_
presents a review of research work on the dendrimer-based catalysis involving the rational design of homogeneous or heterogeneous chiral dendrimer catalysts for enantioselective reactions and the synthesis of catalytically active bimetallic nanoparticles in the presence of dendrimer as a template.
Keywords
References
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Astruc D, Chardac F, Chem. Rev., 101(9), 2991 (2001)
Bae SJ, Kim SW, Hyeon T, Kim BM, Chem. Commun., 31 (2000)
Balogh L, Tomalia DA, J. Am. Chem. Soc., 120(29), 7355 (1998)
Bellocq N, Abramson S, Lasperas M, Brunel D, Moreau P, Tetrahedron: Asymmetry, 10, 3229 (1999)
Bolm C, Derrien N, Seger A, Synlett, 387 (1996)
Bolm C, Zehnder M, Bur D, Angew. Chem.-Int. Edit., 29, 205 (1990)
Bosman AW, Janssen HM, Meijer EW, Chem. Rev., 99(7), 1665 (1999)
Bourque SC, Alper H, Manzer LE, Arya P, J. Am. Chem. Soc., 122(5), 956 (2000)
Bourque SC, Maltais F, Xiao WJ, Tardif O, Alper H, Arya P, Manzer LE, J. Am. Chem. Soc., 121(13), 3035 (1999)
Brunel D, Microporous Mesoporous Mater., 27, 329 (1999)
Chung YM, Rhee HK, Chem. Commun., 238 (2002)
Chung YM, Rhee HK, Catal. Lett., 82(3-4), 249 (2002)
Chung YM, Rhee HK, Catal. Lett., 85(3-4), 159 (2003)
Chung YM, Rhee HK, J. Colloid Interface Sci., submitted (2003)
Chung YM, Rhee HK, J. Mol. Catal. A-Chem., in press (2003)
Chung YM, Rhee HK, C.R. Chimie, submitted (2003)
Coperet C, Chabanas M, Saint-Arroman RP, Basset JM, Angew. Chem.-Int. Edit., 42(2), 156 (2003)
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Creighton JA, Eadon DG, J. Chem. Soc.-Faraday Trans., 87(24), 3881 (1991)
Crooks RM, Lemon BL, Sun L, Yeung LK, Zhao M, Top. Curr. Chem., 212, 81 (2001)
Crooks RM, Zhao M, Sun L, Chechik V, Yeung LK, Accounts Chem. Res., 34(3), 181 (2001)
DeVos DE, Vankelecom IFJ, Jacobs PA, "Chiral Catalyst Immobilization and Recycling," Wiley-VCH, Weinheim (2000)
Esumi K, Suzuki A, Aihara N, Usui K, Torigoe K, Langmuir, 14(12), 3157 (1998)
Esumi K, Suzuki A, Yamahira A, Torigoe K, Langmuir, 16(6), 2604 (2000)
Fendler JH, Korean J. Chem. Eng., 18(1), 1 (2001)
Fischer M, Vogtle F, Angew. Chem.-Int. Edit., 38, 885 (1999)
Floriano PN, Noble CO, Schoonmaker JM, Poliakoff ED, McCarley RL, J. Am. Chem. Soc., 123(43), 10545 (2001)
Gerloch M, Constable EC, "Transition Metal Chemistry: The Valence Schell in d-Block Chemistry," VCH, Weinheim (1994)
Grohn F, Bauer BJ, Akpalu YA, Jackson CL, Amis EJ, Macromolecules, 33(16), 6042 (2000)
Hawker C, Frechet JMJ, J. Am. Chem. Soc., 112(2), 7638 (1990)
Hechet S, Frechet JMJ, Angew. Chem.-Int. Edit., 40(1), 74 (2001)
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Hu QS, Sun C, Monaghan CE, Tetrahedron Lett., 43, 927 (2002)
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King ASH, Twyman LJ, J. Chem. Soc.-Perkin Trans. 1, 2209 (2002)
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Kreiter R, Klej AW, Gebbink RJMK, vanKoten G, Top. Curr. Chem., 217, 163 (2001)
Lewis LN, Chem. Rev., 93, 2693 (1993)
Matthews OA, Shipway AN, Stoddart JF, Prog. Polym. Sci., 23, 1 (1998)
Murota M, Sato S, Tsubokawa N, Polym. Adv. Technol., 13, 144 (2002)
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Newkome GR, Moorefield CN, Vogtle F, "Dendritic Molecules: Concepts, Synthesis, Perspectives," VCH, Weinheim (1996)
Niu YH, Yeung LK, Crooks RM, J. Am. Chem. Soc., 123(28), 6840 (2001)
Oosterom GE, Reek NJH, Kramer PCJ, vanLeeuwen PWNM, Angew. Chem.-Int. Edit., 40(10), 1828 (2001)
Panster P, Wieland S, "Applied Homogeneous Catalysis with Organometallic Compounds 2," Cornils, B. and Hermann, W.A., Eds., Wiley-VCH, Weinheim (1996)
Peerlings HWI, Jansen JFGA, de BV, denBerg EMM, Meijer EW, Polym. Mater. Sci. Eng., 73, 342 (1995)
Peerlings HWI, Meijer EW, Chem. Eur. J., 3(10), 1563 (1997)
Rheiner PB, Seebach D, Chem. Eur. J., 5(11), 3221 (1999)
Sanders-Hovens MSTH, Jansen JFGA, Vekemans JAJM, Meijer EW, Polym. Mater. Sci. Eng., 73, 338 (1995)
Sato I, Hosoi K, Kodaka R, Soai K, Eur. J. Org. Chem., 3115 (2002)
Sato I, Kodaka R, Hosoi K, Soai K, Tetrahedron: Asymmetry, 13, 805 (2002)
Sato I, Kodata R, Shibata T, Hirokawa Y, Shirai N, Ohtake K, Soai K, Tetrahedron: Asymmetry, 11, 2271 (2000)
Sato I, Shibata T, Ohtake K, Kodaka R, Hirokawa Y, Shirai N, Soai K, Tetrahedron Lett., 41, 3123 (2000)
Schmid G, "Cluster and Colloids: From Theory to Applications," VCH, New York (1994)
Scott RWJ, Datye AK, Crooks RM, J. Am. Chem. Soc., 125(13), 3708 (2003)
Seebach D, Beck AK, Heckel A, Angew. Chem.-Int. Edit., 40, 93 (2001)
Seebach D, Marti RE, Hintermann T, Helv. Chim. Acta, 79, 2027 (1997)
Seebach D, Marti RE, Hintermann T, Helv. Chim. Acta, 79, 1710 (1996)
Seebach D, Rheiner PB, Greiveldinger G, Butz T, Sellner H, Top. Curr. Chem., 197, 125 (1998)
Sellner H, Faber C, Rheiner PB, Seebach D, Chem. Eur. J., 6(20), 3692 (2000)
Sellner H, Rheiner PB, Seebach D, Helv. Chim. Acta, 85, 352 (2002)
Sellner H, Seebach D, Angew. Chem.-Int. Edit., 38(13-14), 1918 (1999)
Sinfelt JH, Accounts Chem. Res., 20, 134 (1987)
Soai K, Niwa S, Chem. Rev., 92, 833 (1992)
Soai K, Watanabe M, Yamamoto A, J. Org. Chem., 55, 4832 (1990)
Suzuki T, Hirokawa Y, Ohtake K, Shibata T, Soai K, Tetrahedron: Asymmetry, 8(24), 4033 (1997)
Tomalia DA, Baker H, Dewald J, Hall M, Kallos G, Martin S, Roeck J, Ryder J, Smith P, Polym. J., 17(1), 117 (1985)
Tomalia DA, Durst HD, Top. Curr. Chem., 165, 193 (1993)
Tomalia D, Dvornic PR, Nature, 372(6507), 617 (1994)
Torigoe K, Esumi K, Langmuir, 9, 1664 (1993)
Toshima N, Kushihashi K, Yonezawa T, Hirai H, Chem. Lett., 1769 (1989)
Toshima N, Yonezawa T, Kushihashi K, J. Chem. Soc.-Faraday Trans., 89(14), 2537 (1993)
Tsubokawa N, Ichioka H, Satoh T, Hayashi S, Fujiki K, React. Funct. Polym., 37(1), 75 (1998)
Tsubokawa N, Takayama T, React. Funct. Polym., 43(3), 341 (2000)
Turro N, Barton JK, Tomalia DA, Accounts Chem. Res., 24, 332 (1991)
Twyman LJ, King ASH, Martin IK, Chem. Soc. Rev., 31, 69 (2002)
van Heerbeek R, Kamer PCJ, van Leeuwen PWNM, Reek JNH, Chem. Rev., 102(10), 3717 (2002)
vanKoten G, Jastrzebski JTBH, J. Mol. Catal. A-Chem., 146, 317 (1999)
Watanabe S, Regen SL, J. Am. Chem. Soc., 116(19), 8855 (1994)
Yoon KJ, Kang HK, Yie JE, Korean J. Chem. Eng., 14(5), 399 (1997)
Yoshikawa S, Satoh T, Tsubokawa N, Colloids Surf. A: Physicochem. Eng. Asp., 153, 395 (1999)
Zeng FW, Zimmerman SC, Chem. Rev., 97(5), 1681 (1997)
Zhao M, Crooks RM, Adv. Mater., 11(3), 217 (1999)
Zhao M, Crooks RM, Angew. Chem.-Int. Edit., 38(3), 364 (1999)
Zhao MQ, Sun L, Crooks RM, J. Am. Chem. Soc., 120(19), 4877 (1998)
Zheng J, Stevenson MS, Hikida RS, Van Patten PG, J. Phys. Chem. B, 106(6), 1252 (2002)
Archut A, Vogtle F, "Handbook of Nanostructured Materials and Nanotechnology 5," Nalwa, H.S., Ed., Academic Press, San Diego (2000)
Astruc D, Chardac F, Chem. Rev., 101(9), 2991 (2001)
Bae SJ, Kim SW, Hyeon T, Kim BM, Chem. Commun., 31 (2000)
Balogh L, Tomalia DA, J. Am. Chem. Soc., 120(29), 7355 (1998)
Bellocq N, Abramson S, Lasperas M, Brunel D, Moreau P, Tetrahedron: Asymmetry, 10, 3229 (1999)
Bolm C, Derrien N, Seger A, Synlett, 387 (1996)
Bolm C, Zehnder M, Bur D, Angew. Chem.-Int. Edit., 29, 205 (1990)
Bosman AW, Janssen HM, Meijer EW, Chem. Rev., 99(7), 1665 (1999)
Bourque SC, Alper H, Manzer LE, Arya P, J. Am. Chem. Soc., 122(5), 956 (2000)
Bourque SC, Maltais F, Xiao WJ, Tardif O, Alper H, Arya P, Manzer LE, J. Am. Chem. Soc., 121(13), 3035 (1999)
Brunel D, Microporous Mesoporous Mater., 27, 329 (1999)
Chung YM, Rhee HK, Chem. Commun., 238 (2002)
Chung YM, Rhee HK, Catal. Lett., 82(3-4), 249 (2002)
Chung YM, Rhee HK, Catal. Lett., 85(3-4), 159 (2003)
Chung YM, Rhee HK, J. Colloid Interface Sci., submitted (2003)
Chung YM, Rhee HK, J. Mol. Catal. A-Chem., in press (2003)
Chung YM, Rhee HK, C.R. Chimie, submitted (2003)
Coperet C, Chabanas M, Saint-Arroman RP, Basset JM, Angew. Chem.-Int. Edit., 42(2), 156 (2003)
Cotton A, Wilkinson G, "Advanced Inorganic Chemistry," 5th ed., John Wiley & Sons, New York (1988)
Creighton JA, Eadon DG, J. Chem. Soc.-Faraday Trans., 87(24), 3881 (1991)
Crooks RM, Lemon BL, Sun L, Yeung LK, Zhao M, Top. Curr. Chem., 212, 81 (2001)
Crooks RM, Zhao M, Sun L, Chechik V, Yeung LK, Accounts Chem. Res., 34(3), 181 (2001)
DeVos DE, Vankelecom IFJ, Jacobs PA, "Chiral Catalyst Immobilization and Recycling," Wiley-VCH, Weinheim (2000)
Esumi K, Suzuki A, Aihara N, Usui K, Torigoe K, Langmuir, 14(12), 3157 (1998)
Esumi K, Suzuki A, Yamahira A, Torigoe K, Langmuir, 16(6), 2604 (2000)
Fendler JH, Korean J. Chem. Eng., 18(1), 1 (2001)
Fischer M, Vogtle F, Angew. Chem.-Int. Edit., 38, 885 (1999)
Floriano PN, Noble CO, Schoonmaker JM, Poliakoff ED, McCarley RL, J. Am. Chem. Soc., 123(43), 10545 (2001)
Gerloch M, Constable EC, "Transition Metal Chemistry: The Valence Schell in d-Block Chemistry," VCH, Weinheim (1994)
Grohn F, Bauer BJ, Akpalu YA, Jackson CL, Amis EJ, Macromolecules, 33(16), 6042 (2000)
Hawker C, Frechet JMJ, J. Am. Chem. Soc., 112(2), 7638 (1990)
Hechet S, Frechet JMJ, Angew. Chem.-Int. Edit., 40(1), 74 (2001)
Hu QS, Pugh V, Sabat M, Pu L, J. Org. Chem., 64, 7528 (1999)
Hu QS, Sun C, Monaghan CE, Tetrahedron Lett., 43, 927 (2002)
Jannes G, Dubois V, "Chiral Reactions in Heterogeneous Catalysis," Plenum Press, New York (1993)
Jansen JFGA, Peerlings HWL,de BV, denBerg EMM, Meijer EW, Angew. Chem.-Int. Edit., 34(11), 1206 (1995)
King ASH, Twyman LJ, J. Chem. Soc.-Perkin Trans. 1, 2209 (2002)
Knapen JW, Vandermade AW, Dewilde JC, Vanleeuwen PW, Wijkens P, Grove DM, Vankoten G, Nature, 372(6507), 659 (1994)
Kreiter R, Klej AW, Gebbink RJMK, vanKoten G, Top. Curr. Chem., 217, 163 (2001)
Lewis LN, Chem. Rev., 93, 2693 (1993)
Matthews OA, Shipway AN, Stoddart JF, Prog. Polym. Sci., 23, 1 (1998)
Murota M, Sato S, Tsubokawa N, Polym. Adv. Technol., 13, 144 (2002)
Newkome GR, "Advances in Dendritic Macromolecules," JAI Press Inc., Greenwich (1994)
Newkome GR, Moorefield CN, Vogtle F, "Dendritic Molecules: Concepts, Synthesis, Perspectives," VCH, Weinheim (1996)
Niu YH, Yeung LK, Crooks RM, J. Am. Chem. Soc., 123(28), 6840 (2001)
Oosterom GE, Reek NJH, Kramer PCJ, vanLeeuwen PWNM, Angew. Chem.-Int. Edit., 40(10), 1828 (2001)
Panster P, Wieland S, "Applied Homogeneous Catalysis with Organometallic Compounds 2," Cornils, B. and Hermann, W.A., Eds., Wiley-VCH, Weinheim (1996)
Peerlings HWI, Jansen JFGA, de BV, denBerg EMM, Meijer EW, Polym. Mater. Sci. Eng., 73, 342 (1995)
Peerlings HWI, Meijer EW, Chem. Eur. J., 3(10), 1563 (1997)
Rheiner PB, Seebach D, Chem. Eur. J., 5(11), 3221 (1999)
Sanders-Hovens MSTH, Jansen JFGA, Vekemans JAJM, Meijer EW, Polym. Mater. Sci. Eng., 73, 338 (1995)
Sato I, Hosoi K, Kodaka R, Soai K, Eur. J. Org. Chem., 3115 (2002)
Sato I, Kodaka R, Hosoi K, Soai K, Tetrahedron: Asymmetry, 13, 805 (2002)
Sato I, Kodata R, Shibata T, Hirokawa Y, Shirai N, Ohtake K, Soai K, Tetrahedron: Asymmetry, 11, 2271 (2000)
Sato I, Shibata T, Ohtake K, Kodaka R, Hirokawa Y, Shirai N, Soai K, Tetrahedron Lett., 41, 3123 (2000)
Schmid G, "Cluster and Colloids: From Theory to Applications," VCH, New York (1994)
Scott RWJ, Datye AK, Crooks RM, J. Am. Chem. Soc., 125(13), 3708 (2003)
Seebach D, Beck AK, Heckel A, Angew. Chem.-Int. Edit., 40, 93 (2001)
Seebach D, Marti RE, Hintermann T, Helv. Chim. Acta, 79, 2027 (1997)
Seebach D, Marti RE, Hintermann T, Helv. Chim. Acta, 79, 1710 (1996)
Seebach D, Rheiner PB, Greiveldinger G, Butz T, Sellner H, Top. Curr. Chem., 197, 125 (1998)
Sellner H, Faber C, Rheiner PB, Seebach D, Chem. Eur. J., 6(20), 3692 (2000)
Sellner H, Rheiner PB, Seebach D, Helv. Chim. Acta, 85, 352 (2002)
Sellner H, Seebach D, Angew. Chem.-Int. Edit., 38(13-14), 1918 (1999)
Sinfelt JH, Accounts Chem. Res., 20, 134 (1987)
Soai K, Niwa S, Chem. Rev., 92, 833 (1992)
Soai K, Watanabe M, Yamamoto A, J. Org. Chem., 55, 4832 (1990)
Suzuki T, Hirokawa Y, Ohtake K, Shibata T, Soai K, Tetrahedron: Asymmetry, 8(24), 4033 (1997)
Tomalia DA, Baker H, Dewald J, Hall M, Kallos G, Martin S, Roeck J, Ryder J, Smith P, Polym. J., 17(1), 117 (1985)
Tomalia DA, Durst HD, Top. Curr. Chem., 165, 193 (1993)
Tomalia D, Dvornic PR, Nature, 372(6507), 617 (1994)
Torigoe K, Esumi K, Langmuir, 9, 1664 (1993)
Toshima N, Kushihashi K, Yonezawa T, Hirai H, Chem. Lett., 1769 (1989)
Toshima N, Yonezawa T, Kushihashi K, J. Chem. Soc.-Faraday Trans., 89(14), 2537 (1993)
Tsubokawa N, Ichioka H, Satoh T, Hayashi S, Fujiki K, React. Funct. Polym., 37(1), 75 (1998)
Tsubokawa N, Takayama T, React. Funct. Polym., 43(3), 341 (2000)
Turro N, Barton JK, Tomalia DA, Accounts Chem. Res., 24, 332 (1991)
Twyman LJ, King ASH, Martin IK, Chem. Soc. Rev., 31, 69 (2002)
van Heerbeek R, Kamer PCJ, van Leeuwen PWNM, Reek JNH, Chem. Rev., 102(10), 3717 (2002)
vanKoten G, Jastrzebski JTBH, J. Mol. Catal. A-Chem., 146, 317 (1999)
Watanabe S, Regen SL, J. Am. Chem. Soc., 116(19), 8855 (1994)
Yoon KJ, Kang HK, Yie JE, Korean J. Chem. Eng., 14(5), 399 (1997)
Yoshikawa S, Satoh T, Tsubokawa N, Colloids Surf. A: Physicochem. Eng. Asp., 153, 395 (1999)
Zeng FW, Zimmerman SC, Chem. Rev., 97(5), 1681 (1997)
Zhao M, Crooks RM, Adv. Mater., 11(3), 217 (1999)
Zhao M, Crooks RM, Angew. Chem.-Int. Edit., 38(3), 364 (1999)
Zhao MQ, Sun L, Crooks RM, J. Am. Chem. Soc., 120(19), 4877 (1998)
Zheng J, Stevenson MS, Hikida RS, Van Patten PG, J. Phys. Chem. B, 106(6), 1252 (2002)