RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2006(12): 1793-1815
DOI: 10.1055/s-2006-944221
DOI: 10.1055/s-2006-944221
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Uniform, Non-Natural Oligomers
Weitere Informationen
Received
6 March 2006
Publikationsdatum:
24. Juli 2006 (online)
Publikationsverlauf
Publikationsdatum:
24. Juli 2006 (online)
Abstract
Oligomers with well-defined chain lengths are of interest as foldamers, are important as model compounds for high-molecular-weight polymers and find application in electrooptic and sensory devices. This account presents an overview of the strategies that are available for the synthesis of eight important classes of uniform oligomers. The continuous refinement of the synthetic methods allows the preparation of ever longer oligomers in higher yields and also makes it possible to introduce special functional groups. These improvements could lead to materials with new or improved properties and underline the importance of synthetic organic chemistry for the development of new functional materials.
-
1 Introduction
-
2 Synthetic Strategies
-
3 Alkanes - Oligoenes - Oligoynes
-
4 Oligoesters
-
5 Oligoethers
-
6 Oligo(phenylene)s
-
7 Oligo(phenylene vinylene)s
-
8 Oligo(phenylene ethynylene)s
-
9 Oligopyridines - Oligo(pyridine-pyrimidine)s
-
10 Oligothiophenes
-
11 Conclusions and Outlook
Key words
materials - oligomers - polymers - solid-phase synthesis - supramolecular chemistry
- 1
Van Hest JCM.Tirrell DA. Chem. Commun. 2001, 1897 - 2
Merrifield B. Methods Enzymol. 1997, 289: 3 - 3
Fields GB.Noble RL. Int. J. Pept. Protein Res. 1990, 35: 161 - 4
Heitz W. Chem. Ztg. 1986, 110: 385 - 5
Zahn H.Gleitsman B. Angew. Chem., Int. Ed. Engl. 1963, 2: 410 - 6
Hatada K.Kitayama T.Ute K.Nishiura T. J. Polym. Sci., Part A: Polym. Chem. 2004, 42: 416 - 7
Hatada K.Kitayama T.Ute K.Nishiura T. Macromol. Rapid Commun. 2004, 25: 1447 - 8
Cubberley MS.Iverson BL. Curr. Opin. Chem. Biol. 2001, 5: 650 - 9
Gellman SH. Acc. Chem. Res. 1998, 31: 173 - 10
Hill DJ.Mio MJ.Prince RB.Hughes TS.Moore JS. Chem. Rev. 2001, 101: 3893 - 11
Moore JS.Prince RB. Nonbiological Sequence-Specific Oligomers by Repetitive Synthesis, In Synthesis of PolymersSchlüter AD. Wiley-VCH; Weinheim: 1998. - 12
Ungar G.Stejny J.Keller A.Bidd I.Whiting MC. Science 1985, 229: 386 - 13
Boda E.Ungar G.Brooke GM.Burnett S.Mohammed S.Proctor D.Whiting MC. Macromolecules 1997, 30: 4674 - 14
Paynter OI.Simmonds DJ.Whiting MC. J. Chem. Soc., Chem. Commun. 1982, 1165 - 15
Bidd I.Whiting MC. J. Chem. Soc., Chem. Commun. 1985, 543 - 16
Brooke GM.Burnett S.Mohammed S.Proctor D.Whiting MC. J. Chem. Soc., Perkin Trans. 1 1996, 1635 - 17
Brooke GM.Farren C.Harden A.Whiting MC. Polymer 2001, 42: 2777 - 18
Lee KS.Wegner G. Makromol. Chem., Rapid Commun. 1985, 6: 203 - 19
Martin RE.Diederich F. Angew. Chem. Int. Ed. 1999, 38: 1350 - 20
Spangler CW.McCoy RK.Dembek AA.Sapochak LS.Gates BD. J. Chem. Soc., Perkin Trans. 1 1989, 151 - 21
Spangler CW.Liu P.-K.Dembek AA.Havelka KO. J. Chem. Soc., Perkin Trans. 1 1991, 799 - 22
Duhamel L.Duhamel P.Plé G.Ramondenc Y. Tetrahedron Lett. 1993, 34: 7399 - 23
Kiehl A.Eberhardt A.Adam M.Enkelmann V.Müllen K. Angew. Chem., Int. Ed. Engl. 1992, 31: 1588 - 24
Zeng F.Negishi E. Org. Lett. 2002, 4: 703 - 25
Schwab PFH.Levin MD.Michl J. Chem. Rev. 1999, 99: 1863 - 26
Siemsen P.Livingston RC.Diederich F. Angew. Chem. Int. Ed. 2000, 39: 2633 - 27
Armitage JB.Jones ERH.Whiting MC. J. Chem. Soc. 1951, 44 - 28
Cook CL.Jones ERH.Whiting MC. J. Chem. Soc. 1952, 2883 - 29
Behr OM.Eglinton G.Galbraith AR.Raphael RA. J. Chem. Soc. 1960, 3614 - 30
Hay AS. J. Org. Chem. 1962, 27: 3320 - 31
Eastmond R.Walton DRM. Tetrahedron 1972, 28: 4591 - 32
Eastmond R.Johnson TR.Walton DRM. Tetrahedron 1972, 28: 4601 - 33
Rubin Y.Lin SS.Knobler CB.Anthony J.Boldi AM.Diederich F. J. Am. Chem. Soc. 1991, 113: 6943 - 34
Bartik T.Bartik B.Brady M.Dembinski R.Gladysz JA. Angew. Chem., Int. Ed. Engl. 1996, 35: 414 - 35
Peters TB.Bohling JC.Arif AM.Gladysz JA. Organometallics 1999, 18: 3261 - 36
Dembinski R.Bartik T.Bartik B.Jaeger M.Gladysz JA. J. Am. Chem. Soc. 2000, 122: 810 - 37
Mohr W.Stahl J.Hampel F.Gladysz JA. Chem. Eur. J. 2003, 9: 3324 - 38
Zheng Q.Gladysz JA. J. Am. Chem. Soc. 2005, 127: 10508 - 39
Xu GL.Wang CY.Ni YH.Goodson TG.Ren T. Organometallics 2005, 24: 3247 - 40
Gibtner T.Hampel F.Gisselbrecht JP.Hirsch A. Chem. Eur. J. 2002, 8: 408 - 41
Eisler S.Slepkov AD.Elliott E.Luu T.McDonald R.Hegmann FA.Tykwinski RR. J. Am. Chem. Soc. 2005, 127: 2666 - 42
Hässlin H.-W.Dröscher M.Wegner G. Makromol. Chem. 1980, 181: 301 - 43
Pénisson R.Zahn H. Makromol. Chem. 1970, 133: 25 - 44
Huang B.Hermes ME. J. Polym. Sci., Part A: Polym. Chem. 1995, 33: 1419 - 45
Lengweiler UD.Fritz MG.Seebach D. Helv. Chim. Acta 1996, 79: 670 - 46
Seebach D.Fritz MG. Int. J. Biol. Macromol. 1999, 25: 217 - 47
Krell CM.Seebach D. Eur. J. Org. Chem. 2000, 1207 - 48
Brooke GM.Cameron NR.MacBride JAH.Whiting MC. Polymer 2002, 43: 1139 - 49
Williams JB.Chapman TM.Hercules DM. Macromolecules 2003, 36: 3898 - 50
Kuisle O.Quinoa E.Riguera R. J. Org. Chem. 1999, 64: 8063 - 51
Brummer O.Clapham B.Janda KD. Tetrahedron Lett. 2001, 42: 2257 - 52
Kochendoerfer GG.Chen S.-Y.Mao F.Cressman S.Traviglia S.Shao H.Hunter CL.Low DW.Cagle EN.Carnevali M.Gueriguian V.Keogh PJ.Porter H.Stratton SM.Wiedeke MC.Wilken J.Tang J.Levy JJ.Miranda LP.Crnogorac MM.Kalbag S.Botti P.Schindler-Horvat J.Savatski L.Adamson JW.Kung A.Kent SBH.Bradburne JA. Science 2003, 299: 884 - 53
Burns CJ.Field LD.Morgan J.Petteys BJ.Prashar J.Ridley DD.Sandanayake KRAS.Vignevich V. Aust. J. Chem. 2001, 54: 431 - 54
Teo HH.Mobbs RH.Booth C. Eur. Polym. J. 1982, 18: 541 - 55
Kinugasa S.Hayashi H.Hattori S. Polym. J. 1990, 22: 1059 - 56
Kinugasa S.Takatsu A.Nakanishi H.Nakahara H.Hattori S. Macromolecules 1992, 25: 4848 - 57
Keegstra EMD.Zwikker JW.Roest MR.Jenneskens LW. J. Org. Chem. 1992, 57: 6678 - 58
Malanga C.Spassky N.Menicagli R.Chiellini E. Synth. Commun. 1982, 12: 67 - 59
Malanga C.Spassky N.Menicagli R.Chiellini E. Polym. Bull. 1983, 9: 328 - 60
Henderson HC.Sherrington DC.Gough A. Polymer 1994, 35: 2867 - 61
Knuf EC.Jiang JK.Gin MS. J. Org. Chem. 2003, 68: 9166 - 62
Percec V.Asandei AD. Macromolecules 1997, 30: 7701 - 63
Berresheim AJ.Müller M.Müllen K. Chem. Rev. 1999, 99: 1747 - 64
Kovacic P.Jones MB. Chem. Rev. 1987, 87: 357 - 65
Kraft A.Grimsdale AC.Holmes AB. Angew. Chem. Int. Ed. 1998, 37: 402 - 66
Reddinger JL.Reynolds JR. Adv. Polym. Sci. 1999, 145: 57 - 67
Grimsdale AC.Müllen K. Angew. Chem. Int. Ed. 2005, 44: 5592 - 68
Scherf U. Top. Curr. Chem. 1999, 201: 163 - 69
Deeg O.Kirsch P.Pauluth D.Bäuerle P. Chem. Commun. 2002, 2762 - 70
Sidorov V.Douglas T.Dzekunov SM.Abdallah D.Ghebremariam B.Roepe PD.Matile S. Chem. Commun. 1999, 1429 - 71
Winum J.-Y.Matile S. J. Am. Chem. Soc. 1999, 121: 7961 - 72
Baumeister B.Matile S. Chem. Commun. 2000, 913 - 73
Baumeister B.Sakai N.Matile S. Angew. Chem. Int. Ed. 2000, 39: 1955 - 74
Pummerer R.Bittner K. Ber. Dtsch. Chem. Ges. 1924, 57: 84 - 75
Pummerer R.Seligsberger L. Ber. Dtsch. Chem. Ges. 1931, 64: 2477 - 76
Nozaki T.Tamura M.Harada Y.Saito K. Bull. Chem. Soc. Jpn. 1960, 33: 1329 - 77
Kern W.Seibel M.Wirth HO. Makromol. Chem. 1959, 29: 164 - 78
Cade JA.Pilbeam A. J. Chem. Soc. 1964, 114 - 79
Heitz W.Ullrich R. Makromol. Chem. 1966, 98: 29 - 80
Mayer F.Schiffner R. Ber. Dtsch. Chem. Ges. 1932, 65: 1337 - 81
Müller E.Töpel T. Ber. Dtsch. Chem. Ges. 1939, 72: 273 - 82
Kern W.Gruber W.Wirth HO. Makromol. Chem. 1960, 37: 198 - 83
Kovacic P.Lange RM. J. Org. Chem. 1964, 29: 2416 - 84
Laird T.Ollis WD.Sutherland IO. J. Chem. Soc., Perkin Trans. 1 1980, 1473 - 85
Unroe MR.Reinhardt BA. Synthesis 1987, 981 - 86
Subramaniam G.Gilpin RK. Synthesis 1992, 1232 - 87
Kauffman JM. Synthesis 1999, 918 - 88
Galda P.Rehahn M. Synthesis 1996, 614 - 89
Liess P.Hensel V.Schlüter AD. Liebigs Ann. 1996, 1037 - 90
Read MW.Escobedo JO.Willis DM.Beck PA.Strongin RM. Org. Lett. 2000, 2: 3201 - 91
McDonald FE.Smolentsev V. Org. Lett. 2002, 4: 745 - 92
Tour JM. Chem. Rev. 1996, 96: 537 - 93
Tour JM. Acc. Chem. Res. 2000, 33: 791 - 94
Schenk R.Gregorius H.Meerholz K.Heinze J.Müllen K. J. Am. Chem. Soc. 1991, 113: 2634 - 95
Heinze J.Mortensen J.Müllen K.Schenk R. J. Chem. Soc., Chem. Commun. 1987, 701 - 96
Gregorius H.Baumgarten M.Reuter R.Tyutyulkov N.Müllen K. Angew. Chem., Int. Ed. Engl. 1992, 31: 1653 - 97
Meier H.Gerold J.Kolshorn H.Baumann W.Bletz M. Angew. Chem. Int. Ed. 2001, 41: 292 - 98
Jørgensen M.Krebs FC. J. Org. Chem. 2004, 69: 6688 - 99
Maddux T.Li W.Yu L. J. Am. Chem. Soc. 1997, 119: 844 - 100
Chan TL.Chow HF.Fong S.Leung MK.Tu JG. J. Chem. Soc., Chem. Commun. 1994, 1919 - 101
Siegrist AE. Helv. Chim. Acta 1967, 50: 906 - 102
Siegrist AE.Liechti P.Meyer HR.Weber K. Helv. Chim. Acta 1969, 52: 2521 - 103
Meier H.Ickenroth D. Eur. J. Org. Chem. 2002, 1745 - 104
Zheng J.Swager TM. Adv. Polym. Sci. 2005, 177: 151 - 105
Bunz UHF. Adv. Polym. Sci. 2005, 177: 1 - 106
Ray CR.Moore JS. Adv. Polym. Sci. 2005, 177: 91 - 107
Blatchly RA.Tew GN. J. Org. Chem. 2003, 68: 8780 - 108
Shotwell S.Windscheif PM.Smith MD.Bunz UHF. Org. Lett. 2004, 6: 4151 - 109
Zhang J.Moore JS.Xu Z.Aguirre RA. J. Am. Chem. Soc. 1992, 114: 2273 - 110
Zhang J.Pesak DJ.Ludwick JL.Moore JS. J. Am. Chem. Soc. 1994, 116: 4227 - 111
Stone MT.Moore JS. Org. Lett. 2004, 6: 469 - 112
Schumm JS.Pearson DL.Tour JM. Angew. Chem., Int. Ed. Engl. 1994, 33: 1360 - 113
Jones L.Schumm JS.Tour JM. J. Org. Chem. 1997, 62: 1388 - 114
Jones TV.Blatchly RA.Tew GN. Org. Lett. 2003, 5: 3297 - 115
Ziener U.Godt A. J. Org. Chem. 1997, 62: 6137 - 116
Kukula H.Veit S.Godt A. Eur. J. Org. Chem. 1999, 277 - 117
Lavastre O.Ollivier L.Dixneuf PH.Sibandhit S. Tetrahedron 1996, 52: 5495 - 118
Zhou CZ.Liu T.Xu JM.Chen ZK. Macromolecules 2003, 36: 1457 - 119
Nierengarten J.-F.Gu T.Hadziioannou G.Tsamouras D.Krasnikov V. Helv. Chim. Acta 2004, 87: 2948 - 120
Nelson JC.Young JK.Moore JS. J. Org. Chem. 1996, 61: 8160 - 121
Young JK.Nelson JC.Moore JS. J. Am. Chem. Soc. 1994, 116: 10841 - 122
Huang S.Tour JM. J. Am. Chem. Soc. 1999, 121: 4908 - 123
Huang S.Tour JM. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1998, 39: 525 - 124
Constable EC. Tetrahedron 1992, 48: 10013 - 125
Tschierske C. Angew. Chem. Int. Ed. 2000, 39: 2454 - 126
Constable EC. Prog. Inorg. Chem. 1994, 42: 67 - 127
Albrecht M. Chem. Rev. 2001, 101: 3457 - 128
Hannon MJ.Childs LJ. Supramol. Chem. 2004, 16: 7 - 129
Burstall FH. J. Chem. Soc. 1938, 1662 - 130
Frank RL.Riener EF. J. Am. Chem. Soc. 1950, 72: 4182 - 131
Kröhnke F. Synthesis 1976, 1 - 132
Constable EC.Smith DR. Tetrahedron 1997, 53: 1715 - 133
Potts KT. Bull. Soc. Chim. Belg. 1990, 99: 741 - 134
Potts KT.Cipullo MJ.Ralli P.Theodoridis G. J. Org. Chem. 1982, 47: 3027 - 135
Bassani DM.Lehn J.-M. Bull. Soc. Chim. Fr. 1997, 134: 897 - 136
Bassani DM.Lehn J.-M.Baum G.Fenske D. Angew. Chem., Int. Ed. Engl. 1997, 36: 1845 - 137
Ohkita M.Lehn J.-M.Baum G.Fenske D. Chem. Eur. J. 1999, 5: 3471 - 138
Newkome GR.Patri AK.Holder E.Schubert US. Eur. J. Org. Chem. 2004, 235 - 139
Lehmann U.Henze O.Schlüter AD. Chem. Eur. J. 1999, 5: 854 - 140
Chotalia R.Constable EC.Neuburger M.Smith DR.Zehnder M. J. Chem. Soc., Dalton Trans. 1996, 4207 - 141
Cárdenas DJ.Sauvage J.-P. Synlett 1996, 916 - 142
Hanan GS.Lehn J.-M.Kyritsakas N.Fischer J. J. Chem. Soc., Chem. Commun. 1995, 765 - 143
Benaglia M.Ponzini F.Woods CR.Siegel JS. Org. Lett. 2001, 3: 967 - 144
Roncali J. Chem. Rev. 1992, 92: 711 - 145
McCullough RD. Adv. Mater. 1998, 10: 93 - 146
Mitschke U.Bäuerle P. J. Mater. Chem. 2000, 10: 1471 - 147
McQuade DT.Pullen AE.Swager TM. Chem. Rev. 2000, 100: 2537 - 148
Sease JW.Zechmeister L. J. Am. Chem. Soc. 1947, 69: 270 - 149
Asano T.Ito S.Saito N.Hatakeda K. Heterocycles 1977, 6: 317 - 150
Kagan J.Arora SK. Heterocycles 1983, 20: 1937 - 151
Kagan J.Arora SK. Tetrahedron Lett. 1983, 24: 4043 - 152
Kagan J.Arora SK. J. Org. Chem. 1983, 48: 4317 - 153
Ten Hoeve W.Wynberg H.Havinga EE.Meijer EW. J. Am. Chem. Soc. 1991, 113: 5887 - 154
Tamao K.Kodama S.Nakajima I.Kumada M.Minato A.Suzuki K. Tetrahedron 1982, 38: 3347 - 155
Cunningham DD.Laguren-Davidson L.Mark HB.Van Pham C.Zimmer H. J. Chem. Soc., Chem. Commun. 1987, 1021 - 156
Bäuerle P.Fischer T.Bidlingmeier B.Stabel A.Rabe JP. Angew. Chem., Int. Ed. Engl. 1995, 34: 303 - 157
Nakanishi H.Sumi N.Aso Y.Otsubo T. J. Org. Chem. 1998, 63: 8632 - 158
Tour JM.Wu R. Macromolecules 1992, 25: 1901 - 159
Kirschbaum T.Azumi R.Mena-Osteritz E.Bäuerle P. New J. Chem. 1999, 23: 241 - 160
Spivey AC.Turner DJ.Turner ML.Yeates S. Org. Lett. 2002, 4: 1899 - 161
Sakurai S.Goto H.Yashima E. Org. Lett. 2001, 3: 2379 - 162
Malenfant PRL.Fréchet JMJ. Chem. Commun. 1998, 2657 - 163
Briehn CA.Kirschbaum T.Bäuerle P. J. Org. Chem. 2000, 65: 352 - 164
Briehn CA.Bäuerle P. J. Comb. Chem. 2002, 4: 457 - 165
Kirschbaum T.Briehn CA.Bäuerle P. J. Chem. Soc., Perkin Trans. 1 2000, 8: 1211