Synthesis and characterization of pyrrole and thiophene functional polystyrenes via "click chemistry"

Polymer Bulletin

Volumn 67, Issue 4, 2011, Pages 609-621

  Kiskan, Baris ^a   Gacal, Burcin ^a   Asan, Mirnur ^a   Gunaydin, Emre Comert ^a   Yilmaz, Ismail ^a   Yagci, Yusuf ^a  

^a ISTANBUL TECHNICAL UNIVERSITY   (Turkey)

Author keywords

1,3 Dipolar cycloadditions; Click chemistry; Polystyrene; Pyrrole; Thiophene

Indexed keywords

1 ,3-DIPOLAR CYCLOADDITIONS; AZIDO GROUP; CLICK CHEMISTRY; ESTERIFICATION REACTIONS; HIGH EFFICIENCY; N ,N-DIMETHYLFORMAMIDE; NITROXIDE MEDIATED RADICAL POLYMERIZATION; PROPARGYL; PYRROLE; SIDE-CHAINS;

CYCLIC VOLTAMMETRY; DIMETHYLFORMAMIDE; ESTERIFICATION; ETHERS; NITROGEN COMPOUNDS; PHENOLS; POLYMERS; POLYSTYRENES; SPECTRUM ANALYSIS; STYRENE; SYNTHESIS (CHEMICAL); THIOPHENE;

CYCLOADDITION;

EID: 80051586697     PISSN: 01700839     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00289-010-0412-9     Document Type: Article

References (46)

1. S Bernier S Garreau M Bera-Aberem C Gravel M Leclerc 2002 A versatile approach to affinitychromic polythiophenes J Am Chem Soc 124 12463 12468 10.1021/ja027387l 1:CAS:528:DC%2BD38XntlOqsrg%3D (Pubitemid 35204571)
2. Y Li G Vamvounis S Holdcroft 2002 Control of conjugation length and enhancement of fluorescence efficiency of poly(p-phenylenevinylene)s via post-halogenation Chem Matter 14 1424 1429 10.1021/cm011603s 1:CAS:528:DC%2BD38XhsFait7c%3D
3. Y Li G Vamvounis J Yu S Holdcroft 2001 A novel and versatile methodology for functionalization of conjugated polymers. transformation of poly(3-bromo-4-hexylthiophene) via palladium-catalyzed coupling chemistry Macromolecules 34 3130 3132 10.1021/ma010293w 1:CAS:528:DC%2BD3MXisFemurY%3D (Pubitemid 34220556)
4. HC Kolb MG Finn KB Sharpless 2001 Click chemistry: diverse chemical function from a few good reactions Angew Chem Int Ed 40 2004 2021 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5 1:CAS:528:DC%2BD3MXksVOis78%3D
5. ZP Demko KB Sharpless 2002 A click chemistry approach to tetrazoles by Huisgen 1,3-dipolar cycloaddition: synthesis of 5-sulfonyl tetrazoles from azides and sulfonyl cyanides Angew Chem Int Ed 41 2110 2113 10.1002/1521- 3773(20020617)41:12<2110::AID-ANIE2110>3.0.CO;2-7 1:CAS:528: DC%2BD38XltVWgt7o%3D (Pubitemid 34746918)
6. R Huisgen R Knorr L Möbius G Szeimies 1965 1.3-Dipolare cycloadditionen, XXIII. Einige Beobachtungen zur Addition organischer Azide an CC-Dreifachbindungen Chem Ber 98 4014 4021 10.1002/cber.19650981228 1:CAS:528:DyaF28XislGitw%3D%3D
7. R Huisgen G Szeimies L Möbius 1967 1.3-Dipolare Cycloadditionen, XXXII. Kinetik der Additionen organischer Azide an CC-Mehrfachbindungen Chem Ber 100 2494 2507 10.1002/cber.19671000806 1:CAS:528:DyaF2sXkvF2gur4%3D
8. BN Gacal B Koz B Gacal B Kiskan M Erdogan Y Yagci 2009 Pyrene functional poly(vinyl alcohol) by "click" chemistry J Polym Sci A 47 1317 1326 10.1002/pola.23240 1:CAS:528:DC%2BD1MXitlymsbo%3D
9. B Kiskan G Demiray Y Yagci 2008 Thermally curable polyvinyl chloride via click chemistry J Polym Sci A 46 3512 3518 10.1002/pola.22685 1:CAS:528:DC%2BD1cXmvFWns78%3D
10. WH Binder R Sachsenhofer 2007 'Click' chemistry in polymer and materials science Macromol Rapid Commun 28 15 54 10.1002/marc.200600625 1:CAS:528:DC%2BD2sXhs1Ortrs%3D (Pubitemid 46192085)
11. H Gao K Matyjaszewski 2006 Synthesis of star polymers by a combination of ATRP and the "click" coupling method Macromolecules 39 4960 4965 10.1021/ma060926c 1:CAS:528:DC%2BD28XlvFWmsb0%3D (Pubitemid 44186644)
12. BA Laurent SM Grayson 2006 An efficient route to well-defined macrocyclic polymers via "click" cyclization J Am Chem Soc 128 4238 4239 10.1021/ja0585836 1:CAS:528:DC%2BD28XitlOjur8%3D
13. B Parrish RB Breitenkamp T Emrick 2005 PEG- and peptide-grafted aliphatic polyesters by click chemistry J Am Chem Soc 127 7404 7410 10.1021/ja050310n 1:CAS:528:DC%2BD2MXjs1KjtL8%3D (Pubitemid 40746025)
14. T Liebert C Hänsch T Heinze 2006 Click chemistry with polysaccharides Macromol Rapid Commun 27 208 213 10.1002/marc.200500686 1:CAS:528:DC%2BD28Xhs1ensbk%3D (Pubitemid 43220960)
15. RK Iha KL Wooley AM Nystrom DJ Burke MJ Kade CJ Hawker 2009 Applications of orthogonal "click" chemistries in the synthesis of functional soft materials Chem Rev 109 5620 5686 10.1021/cr900138t 1:CAS:528:DC%2BD1MXhtlymtbvO
16. M Ergin B Kiskan B Gacal Y Yagci 2007 Thermally curable polystyrene via click chemistry Macromolecules 40 4724 4727 10.1021/ma070549j 1:CAS:528:DC%2BD2sXlsFOrsbg%3D (Pubitemid 47110769)
17. M Kukut B Kiskan Y Yagci 2009 Self-curable benzoxazine functional polybutadienes synthesized by click chemistry Des Monomer Polym 12 167 176 10.1163/156855509X412108 1:CAS:528:DC%2BD1MXlsFSqtLY%3D
18. G Temel B Aydogan N Arsu Y Yagci 2009 Synthesis and characterization of one-component polymeric photoinitiator by simultaneous double click reactions and its use in photoinduced free radical polymerization Macromolecules 42 6098 6106 10.1021/ma901162y 1:CAS:528:DC%2BD1MXoslWlsLs%3D
19. MA Tasdelen W Van Camp E Goethals P Dubois F Du Prez Y Yagci 2008 Polytetrahydrofuran/clay nanocomposites by in situ polymerization and "click" chemistry processes Macromolecules 41 6035 6040 10.1021/ma801149x 1:CAS:528:DC%2BD1cXovFSlurc%3D
20. PM Beaujuge JR Reynolds 2010 Color control in pi-conjugated organic polymers for use in electrochromic devices Chem Rev 110 268 320 10.1021/cr900129a 1:CAS:528:DC%2BC3cXivFKrug%3D%3D
21. M Berggren A Richter-Dahlfors 2007 Organic bioelectronics Adv Mater 19 3201 3213 10.1002/adma.200700419 1:CAS:528:DC%2BD2sXht12jt7vJ (Pubitemid 350044459)
22. MA Rahman P Kumar DS Park YB Shim 2008 Electrochemical sensors based on organic conjugated polymers Sensors 8 118 141 10.3390/s8010118 1:CAS:528:DC%2BD1cXksFegurk%3D
23. J Roncali 2007 Molecular engineering of the band gap of π-conjugated systems: facing technological applications Macromol Rapid Commun 28 1761 1775 10.1002/marc.200700345 1:CAS:528:DC%2BD2sXhtVCmtrbO (Pubitemid 47411423)
24. EE Havinga LW Vanhorssen W Tenhoeve H Wynberg EW Meijer 1987 Self-doped water-soluble conducting polymers Polym Bull 18 277 281 10.1007/BF00255122 1:CAS:528:DyaL1cXhsVGjtA%3D%3D
25. N Kizilyar L Toppare A Onen Y Yagci 1999 Synthesis of conducting PPy/pTHF copolymers J Appl Polym Sci 71 713 720 10.1002/(SICI)1097-4628(19990131)71: 5<713::AID-APP5>3.0.CO;2-X 1:CAS:528:DyaK1MXovFGl
26. F Yilmaz L Cianga Y Guner L Topppare Y Yagci 2004 Synthesis and characterization of alternating copolymers of thiophene-containing N-phenyl maleimide and styrene by photoinduced radical polymerization and their use in electropolymerization Polymer 45 5765 5774 10.1016/j.polymer.2004.06.052 1:CAS:528:DC%2BD2cXmt1Wjtrc%3D (Pubitemid 38993449)
27. C Biran L Toppare T Tincer Y Yagci V Harabagiu 2002 Mechanical properties of conducting H-type polysiloxane-polypyrrole graft copolymers and polytetrahydrofuran-polypyrrole block copolymers J Appl Polym Sci 86 1663 1666 10.1002/app.11031 1:CAS:528:DC%2BD38XntFGnsLk%3D
28. Y Yagci L Toppare 2000 Synthesis of conducting block and graft copolymers with polyether segments Macromol Symp 157 29 38 10.1002/1521-3900(200007)157: 1<29::AID-MASY29>3.0.CO;2-3 1:CAS:528:DC%2BD3cXmvFGqsLk%3D
29. S Alkan L Toppare Y Hepuzer Y Yagci 2001 Synthesis and characterization of conducting block copolymers of thiophene-ended polystyrene with polypyrrole Synthetic Met 119 133 134 10.1016/S0379-6779(00)01402-8 1:CAS:528: DC%2BD3MXjsFGrs7w%3D (Pubitemid 32475215)
30. C Ozdilek J Hacaloglu L Toppare Y Yagci 2004 Structural and thermal characterization of PTSA doped polypyrrole-polytetrahydrofuran graft copolymer Synth Met 140 69 78 10.1016/S0379-6779(03)00022-5 1:CAS:528:DC%2BD3sXps1Cis70%3D
31. N Kizilyar U Akbulut L Toppare MY Ozden Y Yagci 1999 Immobilization of invertase in conducting polypyrrole polytetrahydrofuran graft polymer matrices Synth Met 104 45 50 10.1016/S0379-6779(99)00033-8 1:CAS:528:DyaK1MXjsVahtL4%3D
32. D Mecerreyes JA Pomposo M Bengoetxea H Grande 2000 Novel pyrrole end-functional macromonomers prepared by ring-opening and atom-transfer radical polymerizations Macromolecules 33 5846 5849 10.1021/ma0003046 1:CAS:528:DC%2BD3cXkvFSitrk%3D
33. D Mecerreyes R Stevens C Nguyen JA Pomposo M Bengoetxea H Grande 2002 Synthesis and characterization of polypyrrole-graft-poly(epsilon-caprolactone) copolymers: new electrically conductive nanocomposites Synthetic Met 126 173 178 10.1016/S0379-6779(01)00503-3 1:CAS:528:DC%2BD38XhsVagtbc%3D (Pubitemid 34156720)
34. Y Li W Zhang J Chang J Chen G Li Y Ju 2008 'Click' on conducting polymer coated electrodes: a versatile platform for the modification of electrode surfaces Macromol Chem Phys 209 322 329 10.1002/macp.200700436 1:CAS:528:DC%2BD1cXisFSguro%3D
35. TS Hansen AE Daugaard S Hvilsted NB Larsen 2009 Spatially selective functionalization of conducting polymers by "Electroclick" chemistry Adv Mater 21 4483 4486 10.1002/adma.200900980 1:CAS:528:DC%2BD1MXhsFSnu7fO
36. M Artico R Silvestri S Massa AG Loi S Corrias G Piras P Lacolla 1996 2-Sulfonyl-4-chloroanilino moiety: a potent pharmacophore for the anti-human immunodeficiency virus type 1 activity of pyrrolyl aryl sulfones J Med Chem 39 522 530 10.1021/jm950568w 1:CAS:528:DyaK28XmvVyj (Pubitemid 26041464)
37. B Costello P Evans N Guernion NM Ratcliffe PS Sivanand GC Teare 2000 The synthesis of a number of 3-alkyl and 3-carboxy substituted pyrroles; their chemical polymerisation onto poly(vinylidene fluoride) membranes, and their use as gas sensitive resistors Synth Met 114 181 188 10.1016/S0379-6779(00)00250-2
38. AB Sheremetev SM Konkina IL Yudin DE Dmitriev BB Averkiev MY Antipin 2003 (Pyrrol-1-yl)furazans Rus Chem Bull 52 1413 1418 10.1023/A:1024895631593 1:CAS:528:DC%2BD3sXlslShsro%3D (Pubitemid 36922128)
39. S Govindaraji P Nakache V Marks Z Pomerantz A Zaban JP Lellouche 2006 Novel carboxylated pyrrole- and carbazole-based monomers. Synthesis and electro-oxidation features J Org Chem 71 9139 9143 10.1021/jo061531u 1:CAS:528:DC%2BD28XhtFWju7nE (Pubitemid 44845743)
40. AKD Diaw A Yassar D Gningue-Sall JJ Aaron 2008 Synthetic routes, characterization, electrochemical and spectral properties of p-substituted N-phenylpyrroles Arkivoc 17 122 144
41. B Kiskan A Akar N Kizilcan B Ustamehmetoglu 2005 Soluble and conductive copolymers from 1-(hydroxyalkyl) pyrroles J Appl Polym Sci 96 1830 1834 10.1002/app.21069 1:CAS:528:DC%2BD2MXktVSqsrg%3D (Pubitemid 40751478)
42. Pretsch E, Bühlmann P, Affolter C (2000) Structure determination of organic compounds. Springer-Verlag, Berlin, Heidelberg
43. P Ibison PJS Foot JW Brown 1996 Preparation and characterization of polypyrrole, N-substituted with liquid crystalline moieties Synth Met 76 297 300 10.1016/0379-6779(95)03475-Y 1:CAS:528:DyaK28XitlGgsbc%3D (Pubitemid 126338672)
44. RJ Waltman AF Diaz J Bargon 1984 Substituent effects in the electropolymerization of aromatic heterocyclic compounds J Phys Chem 88 4343 4346 10.1021/j150663a030 1:CAS:528:DyaL2cXltFWntrg%3D
45. HB Yildiz S Kiralp L Toppare Y Yagci K Ito 2006 Synthesis of conducting copolymers of thiophene capped poly(ethylene oxide) with pyrrole and thiophene Mater Chem Phys 100 124 127 10.1016/j.matchemphys.2005.12.017 1:CAS:528:DC%2BD28XpvV2gsbc%3D (Pubitemid 44402813)
46. WA Goedel NS Somanathan V Enkelmann G Wegner 1992 Steric effects in 3-substituted polythiophenes: comparing band gap, nonlinear optical susceptibility and conductivity of poly(3-cyclohexylthiophene) and poly(3-hexylthiophene) Makromol Chem 193 1195 1206 10.1002/macp.1992.021930516 1:CAS:528:DyaK38Xkt1Ogtr8%3D