Abstract
This review article summarizes the synthetic efforts in constructing functional hyperbranched macromoleculesfrom acetylenic triple-bond building blocks. Polymerization reactions including polycoupling, polyadditionand polycyclotrimerization have been developed for the synthesis of new hyperbranched polymers such as polyynes,polyenes, polyarylenes and polytriazoles with novel topological structures and electronic conjugations.Polymers with high molecular weights (up to >1 × 106) havebeen obtained in high yields (up to 100%). Whilst their linear counterparts are often intractable, thehyperbranched conjugated polymers are completely soluble in common organic solvents and are hence readilyprocessable by macroscopic techniques. The hyperbranched polymers exhibit an array of functional propertiesincluding strong light emission, stable optical nonlinearity and high photorefractivity. The polymers cangenerate fluorescent images, assemble into supramolecular patterns, and form well-aligned nanotubes. Thepolyynes can be post-functionalized through metal complexation, whose refractive indexes can be manipulatedto a great extent by photoirradiation. The hyperbranched polymer complexes can serve as precursorsto soft ferromagnetic ceramics and as catalysts for carbon nanotube fabrications.
Access provided by Autonomous University of Puebla. Download to read the full chapter text
Chapter PDF
Similar content being viewed by others
References
Flory PJ (1952) J Am Chem Soc 74:2718
Wang F, Wilson MS, Rauh RD, Schottland P, Reynolds JR (1999) Macromolecules 33:4272
Gao C, Yan D (2001) Macromolecules 34:156
Emrick T, Chang HT, Frechet JMJ (1999) Macromolecules 32:6380
Jikei M, Chon SH, Kakimoto M, Kawauchi S, Imase T, Watanabe J (1999) Macromolecules 32:2061
Russo S, Boulares A, da Rin A, Mariani A, Cosulich ME (1999) Macromol Symp 143:309
Ahoni SM (1995) Polym Adv Technol 6:373
Frechet JMJ, Henmi M, Gitsov I, Aoshima S, Leduc M, Grubbs RB (1995) Science 269:1080
Hawker CJ, Frechet JMJ, Grubbs RB, Dao J (1995) J Am Chem Soc 117:10763
Gaynor SG, Edelman SZ, Matyjaszewski K (1996) Macromolecules 29:1079
Dworak A, Walach W, Trzebicka B (1995) Macromol Chem Phys 196:1963
Suzuki M, Yoshida S, Shiraga K, Saegusa T (1998) Macromolecules 31:1716
Magnusson H, Malmström E, Hult A (1999) Macromol Rapid Commun 20:453
Bednarek M, Biedron T, Helinski J, Kaluzynski K, Kubisa P, Penczek S (1999) Macromol Rapid Commun 20:369
Sunder A, Hanselmann R, Frey H, Mülhaupt R (1999) Macromolecules 32:4240
Sunder A, Heinemann J, Frey H (2000) Chem Eur J 6:2499
Hult A, Johansson M, Malström E (1999) Adv Polym Sci 143:1
Voit B (2003) Comptes Rendus Chimie 6:821
Bunz UHF (2001) Acc Chem Res 34:998
Negishi EI, Anastasia L (2003) Chem Rev 103:1979
Bharathi P, Moore JS (1997) J Am Chem Soc 119:3391
Bharathi P, Moore JS (2000) Macromolecules 33:3212
Kim C, Chang Y, Kim JS (1996) Macromolecules 29:6353
Fomina L, Salcedo R (1996) Polymer 37:1723
Hittinger E, Kokil A, Weder C (2004) Angew Chem Int Ed 43:1808
Weder C (2005) Chem Commun, p 5378
Dong YQ, Li Z, Lam JWY, Dong YP, Feng XD, Tang BZ (2005) Chinese J Polym Sci 23:665
Li Z, Qin A, Lam JWY, Dong YQ, Dong YP, Ye C, Williams ID, Tang BZ (2006) Macromolecules 39:1436
Jikei M, Chon SH, Kakimoto M, Kawauchi S, Imase T, Watanabe J (1999) Macromolecules 32:2061
Lin Q, Long TE (2003) Macromolecules 36:9809
Bunz UHF (2000) Chem Rev 100:1605
Onitsuka K, Ohshiro N, Fujimoto M, Takei F, Takahashi S (2000) Mol Cryst Liq Cryst 342:159
Khan MS, Schwartz DJ, Pasha NA, Kakkar AK, Lin B, Raithby PR, Lewis JZ (1992) Anorg Allg Chem 616:121
Häussler M, Zheng R, Lam JWY, Tong H, Dong H, Tang BZ (2004) J Phys Chem B 108:10645
Ogawa T (1995) Prog Polym Sci 20:943
Hay AS (1998) J Polym Sci Part A: Polym Chem 36:505
Hoffmann B, Zanini D, Ripoche I, Burli R, Vasella A (2001) Helv Chim Acta 84:1862
Siemsen P, Livingston RC, Diederich F (2000) Angew Chem Int Ed 39:2632
Klebansky AL, Grachev IV, Kuznetsova OM (1957) J Gen Chem USSR 27:3008
Bohlmann F, Schönowsky H, Inhoffen E, Grau G (1964) Chem Ber 97:794
Hawker CJ, Lee R, Frechét JMJ (1991) J Am Chem Soc 113:4583
Hölter D, Burgath A, Frey H (1997) Acta Polym 48:30
Xiao Y, Wong RA, Son DY (2000) Macromolecules 33:7232
Kwak G, Masuda T (2002) Macromol Rap Commun 23:68
Kwak G, Takagi A, Fujiki M, Masuda T (2004) Chem Mater 16:781
Rao TV, Yamashita H, Uchimaru Y, Sugiyama J, Takeuchi K (2005) Polymer 46:9736
Morgenroth F, Müllen K (1997) Tetrahedron 53:15349
Huisgen R (1984) In: Padwa A (ed) 1,3-Dipolar Cycloadditions: Introduction, Survey, Mechanism. Wiley, New York
Huisgen R, Szeimies G, Moebius L (1967) Chem Ber 100:2494
Kolb HC, Finn MG, Sharpless KB (2001) Angew Chem Int Ed 40:2004
Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596
Scheel A, Komber H, Voit B (2004) Macromol Rapid Commun 25:1175
Voit B (2005) J Polym Sci Part A: Polym Chem 43:2679
Qin A, Haeussler M, Lam JWY, Tse KKC, Tang BZ (2006) Polym Prepr 47(2):681
Chan TR, Hilgraf R, Sharpless KB, Fokin VV (2004) Org Lett 6:2853
Himo F, Lovell T, Hilgraf R, Rostovtsev VV, Noodleman L, Sharpless KB, Fokin VV (2005) J Am Chem Soc 127:210
Zhang L, Chen X, Xue P, Sun HHY, Williams ID, Sharpless KB, Fokin VV, Jia G (2005) J Am Chem Soc 127:15998
Majireck MM, Weinreb SM (2006) J Org Chem 71:8680
Sergeyev VA, Shitikov VK, Chernomordik YA, Korshak VV (1975) Appl Polym Symp 26:237
Sergeyev VA, Shitikov VK, Kurapov AS, Antonova-Antipova IP (1989) Polym Sci USSR 31:1300
Srinrivasan R, Farona MF (1988) Polym Bull 20:359
Chalk AJ, Gilbert AR (1972) J Polym Sci: Part A-1 10:2033
Bracke W (1972) J Polym Sci: Part A-1 10:2097
Xu K, Tang BZ (1999) Chinese J Polym Sci 17:397
Xu K, Peng H, Sun Q, Dong Y, Salhi F, Luo J, Chen J, Hunag Y, Zhang D, Xu Z, Tang BZ (2000) Macromolecules 35:5821
Zheng R, Dong H, Peng H, Lam JWY, Tang BZ (2004) Macromolecules 37:5196
Xu K, Peng H, Huang Y, Xu Z, Tang BZ (2000) Polym Prepr 41(2):1245
Li Z, Lam JWY, Dong YQ, Dong YP, Sung HHY, Williams ID, Tang BZ (2006) Macromolecules 39:6458
Saito S, Yamamoto Y (2000) Chem Rev 100:2901
Lautens M, Klute W, Tam W (1996) Chem Rev 96:49
Melikyan GG, Nicholas KM (1995) In: Stang PJ, Diederich F (eds) Modern Acetylene Chemistry. Wiley, Weinheim, p 99
Schore NE (1991) In: Trost BM, Flemming I (eds) Comprehensive Organic Synthesis. Pergamon, Oxford 5:1129
Vollhardt KPC (1984) Angew Chem Int Ed 23:539
Mori N, Ikeda S, Odashima K (2001) Chem Commun p 181
Tekeuchi R, Tanaka S, Nakaya Y (2001) Tetrahedron Lett 42:2991
Yamamoto Y, Ogawa R, Itoh K (2000) Chem Commun, p 549
Ozerov OV, Ladipo FT, Patrick BO (1999) J Am Chem Soc 121:7941
Johnson ES, Balaich GJ, Rothwell IP (1997) J Am Chem Soc 119:7685
Masuda T, Mouri T, Higashimura T (1980) Bull Chem Soc Jpn 53:1152
Cotton FA, Hall WT (1980) Inorg Chem 19:2352
Bruck MA, Copenhaver AS, Wigley DE (1987) J Am Chem Soc 109:6525
Cotton FA, Hall WT (1981) Inorg Chem 20:1285
Strickler JR, Wexler PA, Wigley DE (1988) Organometallics 7:2067
Cotton FA, Wilkinson G (1988) Advanced Inorganic Chemistry, 5th ed, Chap 19B. Wiley, New York
Jhingan AK, Maier WF (1987) J Org Chem 52:1161
Zheng R, Häussler M, Dong H, Lam JWY, Tang BZ (2006) Macromolecules 39:7973
Häußler M, Lam JWY, Peng H, Zheng R, Tang BZ (2003) Polym Prepr 44(1):1177
Häußler M, Lam JWY, Zheng R, Peng H, Luo J, Chen J, Law CCW, Tang BZ (2003) Comptes Rendus Chimie 6:833
Law CCW, Chen J, Lam JWY, Peng H, Tang BZ (2004) J Inorg Organomet Polym 14:39
Chen J, Peng H, Law CCW, Dong YP, Lam JWY, Williams ID, Tang BZ (2003) Macromolecules 36:4319
Zheng R, Dong H, Tang BZ (2005) In: Abd-El-Azi A, Carraher C, Pittman C, Sheats J, Zeldin M (eds) Macromolecules Containing Metal- and Metal-like Elements. Wiley, New York
Peng H, Luo J, Cheng L, Lam JWY, Xu K, Dong Y, Zhang D, Huang Y, Xu Z, Tang BZ (2002) Opt Mater 21:315
Peng H, Cheng L, Luo J, Xu K, Sun Q, Dong Y, Salhi F, Lee PPS, Chen J, Tang BZ (2002) Macromolecules 35:5349
Peng H, Lam JWY, Tang BZ (2005) Polymer 46:5746
Peng H, Lam JWY, Tang BZ (2005) Macromol Rapid Commun 26:673
Peng H, Zheng R, Dong H, Jia D, Tang BZ (2005) Chin J Polym Sci 23:1
Häußler M, Dong H, Lam JWY, Zheng R, Qin A, Tang BZ (2005) Chin J Polym Sci 23:567
Dong H, Lam JWY, Häußler M, Zheng R, Peng H, Law CCW, Tang BZ (2004) Curr Trends Polym Sci 9:15
Kong X, Lam JWY, Tang BZ (1999) Macromolecules 32:1722
Zheng R, Lam JWY, Peng H, Häußler M, Law CCW, Tang BZ (2003) Polym Prepr 44(2):770
Balasubramanian K, Selvaraj S, Venkataramani PS (1980) Synthesis p 29
Pigge FC, Ghasedi F, Rath NJ (2002) J Org Chem 67:4547
Matsuda K, Nakamura N, Iwamura H (1994) Chem Lett, p 1765
Dong H, Zheng R, Lam JWY, Häußler M, Tang BZ (2004) Polym Prepr 45(2):825
Dong H, Zheng R, Lam JWY, Häußler M, Tang BZ (2005) Macromolecules 38:6382
Saito S, Yamamoto Y (2000) Chem Rev 100:2901
Jikei M, Kakimoto M (2001) Prog Polym Sci 26:1233
Schluter AD, Wegner G (1993) Acta Polym 44:59
Tour JM (1994) Adv Mater 6:190
Johnen NA, Kim HK, Ober CK (1994) ACS Symp Ser 579:298
Kumar U, Neenan TX (1995) ACS Symp Ser 614:4084
Watson MD, Fechtenkotter A, Mullen K (2001) Chem Rev 101:1267
Masuda T, Tang BZ, Higashimura T, Yamaoka H (1985) Macromolecules 18:2369
Badarau C, Wang ZY (2004) Macromolecules 37:147
Armistead JP, Houser EJ, Keller TM (2000) Appl Organomet Chem 14:253
Gandon S, Mison P, Sillion B (1996) ACS Symp Ser 624:306
Rutherford DR, Stille JK, Elliott CM, Reichert VR (1992) Macromolecules 25:2294
Hergenrother PM (1990) In: Kroschwitz JI (ed) Concise Encyclopedia of Polymer Science & Engineering.Wiley, New York, p 5
Beckham HW, Keller TM (2002) J Mater Chem 12:3363
Mochizuki H Hasui T, Kawamoto M, Ikeda T, Adachi C, Taniguchi Y, Shirota Y (2003) Macromolecules 36:3457
Berlman IB (1971) Handbook of Fluorescence Spectra of Aromatic Molecules, 2nd ed. Academic Press, New York
Chen J, Xie Z, Lam JWY, Law CCW, Tang BZ (2003) Macromolecules 36:1108
Tang BZ, Leung SM, Peng H, Yu NT, Su KC (1997) Macromolecules 30:2848
Lee M, Katz HE, Erben C, Gill DM, Gopalan P, Heber JD, McGee DJ (2002) Science 298:1401
Shi Y, Zhang C, Zhang H, Bechtel JH, Dalton LR, Robinson BH, Steier WH (2000) Science 288:119
Burland DM, Miller RD, Walsh CA (1994) Chem Rev 94:31
Marder SR, Cheng LT, Tiemann BG, Friedli AC, Blanchard-Desce M, Perry JW, Skindhøj J (1994) Science 263:511
Dalton LR, Harper AW, Ren A, Wang F, Todorova G, Chen J, Zhang C, Lee M (1999) Ind Eng Chem Res 38:8
Luo J, Ma H, Haller M, Barto RR (2002) Chem Commun, p 888
Seferis JC (1989) Refractive Indices of Polymers. In: Brandrup J, Immergut EH (eds) Polymer Handbook, 3rd ed. Wiley, New York, p VI/451
Mills NJ (1990) In: Kroschwitz JI (ed) Concise Encyclopedia of Polymer Science & Engineering. Wiley, New York, p 683
Xu K, Peng H, Tang BZ (2001) Polym Prepr 42(1):555
Luo Y, Leszyk J, Qian YD, Gergely J, Tao T (1999) Biochemistry 38:6678
Hasegawa M, Horie K (2001) Prog Polym Sci 26:259
Turro NJ (1978) Modern Molecular Photochemistry. In: Benjamin-Cummings Publ. Co. (ed) Modern Molecular Photochemistry. Menlo Park, California
Qu BJ, Xu YH, Shi FW (1992) Macromolecules 25:5215
Kim K-H, Jang S, Harris FW (2001) Macromolecules 34:8925
Hua JL, Lam JWY, Dong H, Wu L, Wong KS, Tang BZ (2006) Polymer 47:18
Wang Y, Bachman M, Sims CE, Li GP, Allbritton NL (2006) Langmuir 22:2719
Kim C, Burrows PE, Forrest SR (2000) Science 288:831
Sirringhaus H, Kawase T, Friend RH, Shimoda T, Inbasekaran M, Wu W, Woo EP (2000) Science 290:2123
Garnier F, Hajlaoui R, Yassar A, Srivastava P (1994) Science 265:1684
Bunz UHF (2006) Adv Mater 18:973
Widawski G, Rawiso M, Francois B (1994) Nature 369:387
Jenekhe SA, Chen XL (1999) Science 283:372
de Boer B, Stalmach U, Nijland H, Hadziioannou G (2000) Adv Mater 12:1581
Srinivasarao M, Collings D, Philips A, Patel S (2001) Science 292:79
Peng J, Han Y, Li B (2004) Polymer 45:447
Tang BZ (2001) Polym News 26:262
Lam JWY, Tang BZ (2005) Acc Chem Res 38:745
Salhi F, Cheuk KKL, Sun Q, Lam JWY, Cha JAK, Li G, Li B, Luo J, Chen J, Tang BZ (2001) J Nanosci Nanotechnol 1:137
Babudri F, Farinola GM, Naso F (2004) J Mater Chem 14:11
Long NJ, Williams CK (2003) Angew Chem Int Ed 42:2586
Bunz UHF (2003) J Organomet Chem 683:269
Newkome GR, He EF, Moorefield CN (1999) Chem Rev 99:1689
Chauhan BPS, Corriu RJP, Lanneau GF, Priou C, Auner N, Handwerker H, Herdtweck E (1995) Organometallics 14:1657
Chan WY, Berenbaum A, Clendenning SB, Lough AJ, Manners I (2003) Organometallics 22:3796
Nishihara H, Kurashina M, Murata M (2003) Macromol Symp 196:27
Altmann M, Bunz UHF (1995) Angew Chem Int Ed 34:569
Häußler M, Lam JWY, Zheng R, Dong H, Tong H, Tang BZ (2005) J Inorg Organomet Polym Mat 15:519
Hendrickx E, Engels C, Schaerlaekens M, Van Steenwinckel D, Samyn C, Persoons A (2002) J Phys Chem B 106:4588
Lu C, Guan C, Liu Y, Cheng Y, Yang B (2005) Chem Mater 17:2448
Tang BZ, Geng Y, Lam JWY, Li B, Jing X, Wang X, Wang F, Pakhomov AB, Zhang XX (1999) Chem Mater 11:1581
O'Handley RC (2000) Modern Magnetic Materials: Principles and Applications. Wiley, New York, p 491
Sun Q, Xu K, Peng H, Zheng R, Häußler M, Tang BZ (2003) Macromolecules 36:2309
Sun Q, Lam JWY, Xu K, Xu H, Cha JAK, Zhang X, Jing X, Wang F, Tang BZ (2000) Chem Mater 12:2617
Häußler M, Sun Q, Xu K, Lam JWY, Dong H Tang BZ (2005) J Inorg Organomet Polym 15:67
Chatterjee AK, Sharon M, Baneriee R, Neumann-Spallart M (2003) Electrochim Acta 48:3439
Huang ZP, Wang DZ, Wen JG, Sennett M, Gibson H, Ren ZF (2002) Appl Phys A 74:387
Deck CP, Vecchio K (2006) Carbon 44:267
Häußler M, Tse KC, Lam JWY, Tong H, Qin A, Tang BZ (2006) Polym Mat Sci Eng 95:213
Lu JQ, Kopley TE, Moll N, Roitman D, Chamberlin D, Fu Q, Liu J, Russell TP, Rider DA, Manners I, WinnikMA (2005) Chem Mater 17:2227
Lu JQ, Rider DA, Onyegam E, Wang H, Winnik MA, Manners I, Cheng Q, Fu Q, Liu J (2006) Langmuir 22:5174
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2007 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Häußler, M., Tang, B.Z. (2007). Functional Hyperbranched Macromolecules Constructed from Acetylenic Triple-Bond Building Blocks. In: Functional Materials and Biomaterials. Advances in Polymer Science, vol 209. Springer, Berlin, Heidelberg. https://doi.org/10.1007/12_2007_112
Download citation
DOI: https://doi.org/10.1007/12_2007_112
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-71508-5
Online ISBN: 978-3-540-71509-2
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)