Ring-Opening Metathesis Polymerization

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Ring-Opening Metathesis Polymerization (ROMP) Supervisor : Prof. Ru-Jong Jeng Student : I-Chun Tang Date : 2013.12.20. P. Dubois, O. Coulembier and J.-M. Raquez, Handbook of Ring-Opening Polymerization.

Outline Chemistry of ROMP Living ROMP Ring-opening mechanism Chain-transfer reaction Living ROMP Well-defined catalysts and application Schrock-type initiators Grubbs-type initiators Recent application of ROMP Novel catalysts High and low ring-strain monomers Stereoselective and regioselective ROMP Conclusion

C.W. Bielawski , R.H. Grubbs , Prog. Polym. Sci. 32 (2007) 1–29 ROMP Mechanism C.W. Bielawski , R.H. Grubbs , Prog. Polym. Sci. 32 (2007) 1–29

Chain-Transfer Reaction C.W. Bielawski , R.H. Grubbs , Prog. Polym. Sci. 32 (2007) 1–29

Outline Chemistry of ROMP Living ROMP Ring-opening mechanism Chain-transfer reaction Living ROMP Well-defined catalysts and application Schrock-type initiators Grubbs-type initiators Recent application of ROMP Novel catalysts High and low ring-strain monomers Stereoselective and regioselective ROMP Conclusion

C.W. Bielawski , R.H. Grubbs , Prog. Polym. Sci. 32 (2007) 1–29 Living ROMP Characteristics : fast and complete initiation exhibits a linear relationship between the degree of polymerization (typically measured as the number-average molecular weight of the polymer, Mn) and monomer consumption (3) PDI<1.5 Catalysts : convert to growing polymer chains quantitatively and rapidly react with accessible terminating agents to facilitate selective end-functionalization display good solubilities in common organic solvents show high stability toward moisture, air, and common organic functional groups C.W. Bielawski , R.H. Grubbs , Prog. Polym. Sci. 32 (2007) 1–29

C.W. Bielawski , R.H. Grubbs , Prog. Polym. Sci. 32 (2007) 1–29 Living ROMP C.W. Bielawski , R.H. Grubbs , Prog. Polym. Sci. 32 (2007) 1–29

Outline Chemistry of ROMP Living ROMP Ring-opening mechanism Chain-transfer reaction Living ROMP Well-defined catalysts and application Schrock-type initiators Grubbs-type initiators Recent application of ROMP Novel catalysts High and low ring-strain monomers Stereoselective and regioselective ROMP Conclusion

Schrock-Type Initiators Richard R. Schrock (1945 - ) Organic chemistry Metathesis reaction Nobel prize in chemistry (2005) Schrock-Type Initiators Schrock , R.R. , Murdzek , J.S. , Bazan, G.C. , Robbins , J. , DiMare , M. and O ’ Regan , M. ( 1990 ) Journal of the American Chemical Society , 112 , 3875 – 86 .

Grubbs-Type Initiators Robert Howard Grubbs (1942 - ) Methods in organic synthesis The development of metathesis Nobel prize in chemistry (2005) Grubbs-Type Initiators Hoveyda-Grubbs Catalyst Grubbs , R.H. ( 2003 ) Handbook of Metathesis , Vols 1 – 3 , 1st edn (ed. R.H. Grubbs ), Wiley – VCH Verlag GmbH , Weinheim .

C.W. Bielawski , R.H. Grubbs , Prog. Polym. Sci. 32 (2007) 1–29 Catalysts Comparison Schrock (1990) Grubbs (1995) Highly reactive. Poor tolerance in functional group. The catalytic activity increases with the electron withdrawing nature of the two alkoxy ligands. Metathesis of tri- and tetra-substituted olifens is possible. Tolerance in functional group. (CO, OH, NH) Selectivity towards sterically unhindered olefins and strained olefins. Tri- and tetra-substituted olifens are not attacked.. C.W. Bielawski , R.H. Grubbs , Prog. Polym. Sci. 32 (2007) 1–29

Nobel Prize in Chemistry (2005) “ for the development of the metathesis method in organic synthesis " Robert Howard Grubbs (1942 - ) ; USA Field: organic chemistry Methods in organic synthesis The development of metathesis Nobel prize in chemistry (2005) Richard R. Schrock (1945 - ) ; USA Field: organic chemistry Organic chemistry Metathesis reaction Nobel prize in chemistry (2005) Yves Chauvin (1930 - ) ; Belgium Field: organic chemistry Metathesis Nobel prize in chemistry (2005)

Outline Chemistry of ROMP Living ROMP Ring-opening mechanism Chain-transfer reaction Living ROMP Well-defined catalysts and application Schrock-type initiators Grubbs-type initiators Recent application of ROMP Novel catalysts High and low ring-strain monomers Stereoselective and regioselective ROMP Conclusion

Coordination Chemistry Reviews , 249 , 3055 – 74 . Novel Catalysts Opstal , T. , Couchez , K. and Verpoort , F. ( 2003 ) Advanced Synthesis Catalysis , 345 , 393 – 401 . Drozdzak , R. , Allaert , B. , Ledoux , N. ,Dragutan , I. , Dragutan , V. And Verpoort , F. ( 2005 ) Coordination Chemistry Reviews , 249 , 3055 – 74 . Love , J.A. , Morgan , J.P. , Trnka , T.M. and Grubbs , R.H. ( 2002 ) Angewandte Chemie , 114 , 4207 – 9 Frech , C.M. , Blacque , O. , Schmalle , H.W. , Berke , H. , Adlhart , C. and Chen , P. ( 2006 ) Chemistry – A European Journal , 12 , 3325 – 38 .

High and Low Ring-Strain Monomers Singh , R. , Czekelius , C. and Schrock , R.R. ( 2006 ) Macromolecules , 39 , 1316 – 7 . Lee , J.C. , Parker , K.A. and Sampson , N.S. ( 2007 ) Journal of the American Chemical Society , 128 , 4578 – 9 . Hejl , A. , Scherman , O.A. and Grubbs , R.H. ( 2005 ) Macromolecules , 38 , 7214 – 18 .

Stereoselective and Regioselective ROMP Scherman , O.A. , Walker , R. and Grubbs , R.H. ( 2005 ) Macromolecules , 38 , 9009 – 14 . Yang , H. , Islam , M. , Budde , C. and Rowan , S.J. ( 2003 ) Journal of Polymer Science Part A – Polymer Chemistry , 41 ,2107 – 16 . Wang , D. , Yang , L. , Decker , U. ,Findeisen , M. and Buchmeiser , M.R. ( 2005 ) Macromolecular Rapid Communications , 26 , 1757 – 62 . Lehman , S.E. , Jr. , Wagener , K.B. , Baugh ,L.S. , Rucker , S.P. , Schulz , D.N et al.( 2007 ) Macromolecules , 40 , 2643 – 56 .

Outline Chemistry of ROMP Living ROMP Ring-opening mechanism Chain-transfer reaction Living ROMP Well-defined catalysts and application Schrock-type initiators Grubbs-type initiators Recent application of ROMP Novel catalysts High and low ring-strain monomers Stereoselective and regioselective ROMP Conclusion

Conclusion Advantages Prospects Well-defined catalysts Living ROMP → a narrow PDI → tunable sizes, shapes, and functions. Configuration control Prospects Recycling and reusing the precious metal (Mo . Ru …) Further progress in both polymer and materials science. (to break up the limitation of ROMP)

Thanks for your listening !