FTIR. Applications of FTIR in Solid2Phase Organic Synthesis. Vol. 17 No. 5 Sep., 2005 PROGRESS IN CHEMISTRY ( ) : O ; O621.

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1 PROGRESS IN CHEMISTRY Vol. 17 No. 5 Sep FTIR 3 3 ( ) : O ; O : A : X(2005) Applications of FTIR in Solid2Phase Organic Synthesis Huang Qiang Long Quan Zheng Baozhong 3 3 (Department of Materials Science and Engineering Yunnan University Kunming China) Abstract Recent Progress in the applications of transmission diffuse reflectance attenuated total reflection photoacoustic and microscopic Fourier2transform infrared spectroscopy for qualitative and quantitative analyses in solid2 phase organic synthesis is reviewed. Key words combinatorial chemistry ; solid2phase organic synthesis ; FTIR [1 (SPOS) 3 ] (MAS2NMR) [12 13 ] [4 7 ] [8 ] [14 ; (SPIMS) 16 ] [9 ] SPOS [10 ] SPOS SPOS MAS2 (TLC) ( HPLC) NMR SPIMS (cleave (FTIR) and analyze) [11 ] [17 ] SPOS IR : ; : : (No ) (No. 2000YP04) 3 3 e2mail : edu. cn

2 ; SPOS FTIR SPOS FTIR SPOS Yan [18 ] : SPOS FTIR TLC 3 : ( transmission ) ( reflectance ) (photoacoustic ) (micro2ftir) SPOS FTIR FTIR FTIR Scheme 1 KBr IR Sarhan [20 ] IR Merrifield ( scheme 2) 5mg KBr Merrifield FTIR SPOS ( PS2DVB Merifield Wang C O (1 695cm - 1 ) ) (1 595cm - 1 ) ( PS2PEGTentaGel ) C O C IR ( < 2m) (1 150cm - 1 ) PS2PEG FTIR (1 595cm - 1 ) [17 ] Gordeev [19 ] KBr FTIR 9 m n 1 42 (1 42dihydropyridine DHP) 6 (scheme 1) 3 FTIR 1 735cm cm cm - 1 DHP 4 3 Scheme 2 13 C2NMR Gordeev KBr FT2IR FTIR

3 5 FTIR 891 : (1) KBr Arsequell [24 ] ; (2) (S H) (2 555cm - 1 ) ; (3) KBr ; (4) FTIR 1. FTIR DRIETS Goswami [25 ] DRIETS ; O 3 Si (CH 2 β 3 (spacer) (DHAQ) ( scheme 4) 14 C O C N (1 630cm - 1 ) ( FTIR 1 345cm - 1 ) FTIR (DRIFTS) SPOS : (1) ; (2) [21 3mg Deben ] 015 1mg ; (3) ; (4) ; (5) SPOS PS PS2PEG Scheme 3 Scheme 4 150m IR 2m 2. (attenuated total reflectance ATR) 2m KBr (internal reflection) IR [22 ] Sofia [23 ; DRIFTS (2 108cm - 1 ) TentaGel IR ART2FTIR (scheme 3) DRIFTS KBr (30 s) ART2FTIR : (1)

4 SynPhase TM ; (2) IR ; (3) IR ; (4) FTIR ART2FTIR SPOS [17 18 ] Karavoltsos [26 ] Micro2FTIR 15 N C 16 (DIPEA) 17 ( scheme 5) ART2FTIR (1 814cm - 1 ) ATR (1 712cm - 1 ) 1. Scheme 5 ATR2FTIR SPOS IR Gears Crowns Lanterns ( single2bead [27 28 ] FTIR) Yan [32 ] : Mimotopes SynPhase TM [29 30 ] Merrifield Gears Crowns Lanterns SynPhase TM SynPhase TM IR SynPhase TM Yan [31 ] (scheme 6) 3 450cm cm cm cm cm cm - 1 ART2FTIR Scheme 6

5 5 FTIR 893 Gly2Gly2Gly 24 2 IR Fmoc d 9 2Boc 25 Merrifield Wang Rink (Fmoc2Lys2(Boc2d 9 )2OH) (C D) ( 2 TentaGel cm - 1 ) IR Merrifield [33 ] S N 2 TentaGel Wang Yan [34 ] Wang 21 2 ( site2site interaction) (scheme 7) 2 10 Wang (1 795cm - 1 ) (1 728cm - 1 ) ; Wang [ ] SPOS SPOS (spacer) SPOS IR Scheme 7 (scheme 8) Scheme 8 IR SPOS Yan [38 ] 3 SPOS SPOS IR 2. ATR Huber [39 ] ATR SPOS ATR Yan (314mmolg - 1 ) Merrifield Russell 7 (scheme 9) [35 ] KBr 27 ( C N )

6 KBr ATR 100m ATR Scheme 9 Gosselin [40 ] (1 645cm - 1 ) (N H + ) (3 200 cm - 1 ) (scheme 10) 33 (1 741cm cm - 1 ) p2 34 (1 674cm - 1 ) 28 IR (2 231cm - 1 ) (N H) (3 413 cm - 1 ) ; (1 678cm - 1 ) ( C S C) (1 250cm - 1 ) ( O S O ) (1 325cm cm - 1 ) ATR (1 429cm - 1 ) (1 741cm cm - 1 ) 40 5 % Huber ( ATR ) ( 100m) IR Scheme 10 Michelson ( PA2FTIR) DRITTS ATR PA2FTIR IR PA2FTIR

7 5 FTIR 895 ( m2cpba) 34 [ 3 ] 35 ( O S O ) (1 140cm - 1 ) ; 1 82 [51410 ] 272(DBU) ( O S O ) (1 140cm - 1 ) ATR PA2FTIR PA2FTIR Basso [41 ] PA2FTIR Lantern2HMPA(42hydroxymethylphenoxyacetic acid) 37 N2Fmoc ( N2Fmoc2Phe) Passerini ( scheme 11) (2 150cm - 1 ) (1 705cm - 1 ) (1 670cm - 1 ) Scheme 11 FTIR TLC 536 FTIR [ 1 ] James I W. Tetrahedron : [ 2 ] (Xu J X). (Chin. J. Org. Chem. ) : 1 10 (Li W Z) ( Yun L H). (Chin. J. Org. Chem. ) : [ 4 ] Thompson L A Ellman J A. Chem. Rev : [ 5 ] Dewitt D H Czarnik A W. Acc. Chem. Res : [ 6 ] Franzen R G. J. Comb. Chem : [ 7 ] Dolle R E. J. Comb. Chem : [ 8 ] Petsko G A. Nature : 7 14 [ 9 ] ( Xu J ). ( Progress in Chemistry) : [10] (Xu J X) (Ma Y). ( Chemistry) 2002 (3) : [11] Kay C Lorthioir O E Parr N J et al. Biotechnol. Bioeng. (Comb. Chem. ) 2000Π : [12] Keifer P A. J. Org. Chem : [13] Ferngndez2Forner D Huerta J M Ferrer M et al. Tetrahedron Lett : [14] Egner B J Langley GJ Bradley M. J. Org. Chem : [15] Egner B J Bradle M. Tetrahedron : [16] Roice M Kumar K S Pillai V N R. Tetrahedron : [17] Dal Cin M Marchioro C Passarini M et al. IL Farmaco : [18] Yan B Gremlich H U. J. Chromatography B : [19] Gordeev M F Patel D V Gordon E M. J. Org. Chem : [20] Sarhan A A Abdelaal M Y Ali M M et al. Polymer : [21] Deben I Goorden J van Doornum E et al. Eur. J. Org. Chem [22] (Wu Q) ( Yang S Z) (Luo J T). (Spectroscopy and Spectral Analysis) : [23] Chan T Y Chen R Sofia M J et al. Tetrahedron Lett : [24] Arsequell G Gonzglez A Valencia G. Tetrahedron Lett : [25] Goswami A Singh A K. Talanta : [26] Karavoltsos M Mourtas S Gatos D et al. Tetrahedron Lett : [27] Gremlich H U Berets S L. Appl. Spectrosc : 532 [28] Bedos P Feliu L Martinez J. Tetrahedron Lett : [29] Rasoul F Ercole F Pham Y et al. Biopolym : [30] Ede N J. J. Immunol. Meth : 3 11 [31] Yan B Kumaravel G Anjaria H et al. J. Org. Chem : [32] Yan B Kumaravel G. Tetrahedron :

8 [33] Yan B Fell J B Kumaravel G. J. Org. Chem : [34] Yan B Sun Q. J. Org. Chem : [35] Russell K Cole D C McLaren F M et al. J. Am. Chem. Soc : [36] Yan B. Acc. Chem. Res : [37] Yan B. Curr. Opin. Chem. Biol : [38] Yan B Yan H. J. Comb. Chem : [39] Huber W Bubendorf A Grieder A et al. Analytica Chimica Acta : [40] Gosselin F Renzo M D Ellis T H et al. J. Org. Chem : [41] Basso A Banfi L Riva R et al. Tetrahedron Lett : Janh2Teller () ( ) PEMFC ( ) ( ) ( ) ( ) ( ) SnO 2 TiO 2 ( ) ( ) ( ) Al 30 ( ) ( ) ( ) ( ) ( ) ( ) ( ) ( ) (ATRP) ( ) ( ) ( ) ( ) HPLC ( ) ( )