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Polycondensation for Synthesis of Multi-Functional Products

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Miyaura-Suzuki type polycondensation with no use of n-BuLi for preparation of precursors was carried out to obtain a series of p-conjugated materials having multi-functionality. Bully substituent in the monomer restricts propagation in the polycondensation to give high molecular weight products. Although the products thus obtained show low molecular weight, the resultant materials show good optical absorption and fluorescence.


International Letters of Chemistry, Physics and Astronomy (Volume 65)
Z. Y. Qin and H. Goto, "Polycondensation for Synthesis of Multi-Functional Products", International Letters of Chemistry, Physics and Astronomy, Vol. 65, pp. 1-10, 2016
Online since:
Apr 2016

[1] U. Mitschke, P. Bäuerle, The electroluminescence of organic materials, J. Mater. Chem. 10 (2000) 1471-1507.

[2] C. J. Brabec, N. S. Sariciftci, J. C. Hummelen, Plastic solar cells, Adv. Funct. Mater. 11 (2001) 15-26.

DOI: 10.1002/1616-3028(200102)11:1<15::aid-adfm15>;2-1

[3] C.L. Zhu, L.B. Liu, Q. Yang, F.T. Lv, S. Wang, Water-soluble conjugated polymers for imaging, diagnosis, and therapy, Chem. Rev. 112 (2012) 4687–4735.

DOI: 10.1021/cr200263w

[4] S.W. Thomas, G.D. Joly, T.M. Swager, Chemical sensors based on amplifying fluorescent conjugated polymers, Chem. Rev. 107 (2007) 1339-1386.

DOI: 10.1021/cr0501339

[5] E. Roberts, A. N. Sokolov, Z. Bao, Material and device considerations for organic thin-film transistor sensors, J. Mater. Chem. 19 (2009) 3351-3363.

DOI: 10.1039/b816386c

[6] L. Groenendaal, G. Zotti, P. H. Aubert, S. M. Waybright, J. R. Reynolds, Electrochemistry of Poly (3, 4‐alkylenedioxythiophene) Derivatives, Adv. Mater. 15 (2003) 855-879.

DOI: 10.1002/adma.200300376

[7] T. Yokozawa, H. Kohno, Y. Ohta, A. Yokoyama, Catalyst-Transfer Suzuki−Miyaura Coupling Polymerization for Precision Synthesis of Poly (p-phenylene), Macromolecules. 43 (2010) 7095–7100.

DOI: 10.1021/ma101073x

[8] M. Horie, L. A. Majewski, M. J. Fearn, C. Y. Yu, Y. Luo, A. Song, B. R. Saunders, M. L. Turner, Cyclopentadithiophene based polymers—a comparison of optical, electrochemical and organic field-effect transistor characteristics, J. Mater. Chem. 20 (2010).

DOI: 10.1039/b924126d

[9] Y. Liu, X. Chen, J. Qin, G. Yu, Y. Liu, New linear π-conjugated polymers via Suzuki coupling of (1Z, 3Z)-1, 4-dibromo-1, 4-diaryl-buta-1, 3-diene with aromatic diborates: Synthesis and photophysical properties, Polymer. 51 (2010) 3730–3735.

DOI: 10.1016/j.polymer.2010.06.003

[10] N. Miyaura, A. Suzuki, Palladium-catalyzed cross-coupling reactions of organoboron compounds, Chem. Rev. 95 (1995) 2457-2483.

DOI: 10.1021/cr00039a007

[11] A. Suzuki, Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998, J. Organomet. Chem. 576 (1999) 147-168.

DOI: 10.1016/s0022-328x(98)01055-9

[12] S. D. Walker, T. E. Barder, J. R. Martinelli, S. L. Buchwald, A rationally designed universal catalyst for Suzuki–Miyaura coupling processes, Angew. Chem. Int. Ed 43 (2004) 1871-1876.

DOI: 10.1002/anie.200353615

[13] A. Dumas, C. D. Spicer, Z. Gao, T. Takehana, Y. A. Lin, T. Yasukohchi, B. G. Davis, Self‐Liganded Suzuki–Miyaura Coupling for Site‐Selective Protein PEGylation, Angew. Chem. Int. Ed. 52 (2013) 3916–3921.

DOI: 10.1002/ange.201208626

[14] S. P. Stanforth, Catalytic cross-coupling reactions in biaryl synthesis, Tetrahedron 54 (1998) 263-303.

DOI: 10.1016/s0040-4020(97)10233-2

[15] L. A. Thompson, J. A. Ellman, Synthesis and applications of small molecule libraries, Chem. Rev. 96 (1996) 555-600.

[16] S. C. Matthew, B. W. Glasspoole, P. Eisenberger, C. M. Crudden, Synthesis of Enantiomerically Enriched Triarylmethanes by Enantiospecific Suzuki–Miyaura Cross-Coupling Reactions, J. Am. Chem. Soc. 136 (2014) 5828-5831.

DOI: 10.1021/ja412159g

[17] J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M. Lemaire, Aryl-aryl bond formation one century after the discovery of the Ullmann reaction, Chem. Rev. 102 (2002) 1359-1469.

DOI: 10.1021/cr000664r

[18] J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, Highly active palladium catalysts for Suzuki coupling reactions, J. Am. Chem. Soc. 121 (1999) 9550-9561.

DOI: 10.1021/ja992130h

[19] N. Miyaura, T. Yanagi, A. Suzuki, The palladium-catalyzed cross-coupling reaction of phenylboronic acid with haloarenes in the presence of bases, Synth. Commun. 11 (1981) 513-519.

DOI: 10.1080/00397918108063618

[20] N. Miyaura, A. Suzuki, Palladium-catalyzed cross-coupling reactions of organoboron compounds, Chem. Rev. 95 (1995) 2457-2483.

DOI: 10.1021/cr00039a007

[21] G. He, L. Kang, D. W. Torres, O. Shynkaruk, M. Ferguson, R. McDonald, E. Rivard, The Marriage of Metallacycle Transfer Chemistry with Suzuki-Miyaura Cross-Coupling To Give Main Group Element-Containing Conjugated Polymers, J. Am. Chem. Soc. 135 (2013).

DOI: 10.1021/ja402242z

[22] W. Ma, P. K. Iyer, X. Gong, B. Liu, D. Moses, G. C. Bazan, A. J. Heeger, Water/methanol-soluble conjugated copolymer as an electron-transport layer in polymer light-emitting diodes, Adv. Mater. 17 (2005) 274-277.

DOI: 10.1002/adma.200400963

[23] A. Satrijo, T. M. Swager, Facile control of chiral packing in poly (p-phenylenevinylene) spin-cast films, Macromolecules. 38 (2005) 4054-4057.

DOI: 10.1021/ma047418s

[24] J. N. Wilson, W. Steffen, T. G. McKenzie, G. Lieser, M. Oda, D. Neher, U. H. F. Bunz, Chiroptical Properties of Poly(p-phenyleneethynylene) Copolymers in Thin Films: Large g-Values, J. Am. Chem. Soc. 124 (2002) 6830-6831.

DOI: 10.1021/ja026532s

[25] A. Kimyonok, E. Tekin, G. Haykır, F. Turksoy, Synthesis, photophysical and electroluminescence properties of anthracene-based green-emitting conjugated polymers, J. Lumin. 146 (2014) 186-192.

DOI: 10.1016/j.jlumin.2013.09.034
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