Toward the synthesis of strongly photoluminescing polyesters by entropically driven ring-opening polymerizations
Richard T. Williams
Organic Materials Innovation Centre, School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK
Search for more papers by this authorCorresponding Author
Philip Hodge
Organic Materials Innovation Centre, School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK
Organic Materials Innovation Centre, School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL.Search for more papers by this authorCorresponding Author
Stephen G. Yeates
Organic Materials Innovation Centre, School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK
Organic Materials Innovation Centre, School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL.Search for more papers by this authorRichard T. Williams
Organic Materials Innovation Centre, School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK
Search for more papers by this authorCorresponding Author
Philip Hodge
Organic Materials Innovation Centre, School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK
Organic Materials Innovation Centre, School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL.Search for more papers by this authorCorresponding Author
Stephen G. Yeates
Organic Materials Innovation Centre, School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK
Organic Materials Innovation Centre, School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL.Search for more papers by this authorAbstract
A range of strongly fluorescent polyesters incorporating distyrylarylene moieties have been prepared. The polyesters have the potential to be prepared from the corresponding macrocyclic oligomers (MCOs) by entropically driven ring-opening polymerizations (ED-ROP). This reactive macrocyclic oligomer approach to the polymers has the advantage of allowing the deposition of conjugated materials by solution deposition techniques, such as ink-jet, since the macrocycles after deposition can be converted directly on the substrate, in the absence of any external initiator, into solvent intractable thin polymeric films. Copyright © 2008 John Wiley & Sons, Ltd.
REFERENCES
- 1 De Gens BJ, Duineveld PC, Schubert US. Inkjet printing of polymers: state of the art and future developments. Adv. Mater. 2004; 16: 203–213.
- 2 Xu D, Sanchez-Romaguera V, Barbosa S, Travis W, de Wit J, Swan P, Yeates SG. Inkjet printing of polymer solutions and the role of chain entanglement. J. Mater. Chem. 2007; 17: 4902–4907.
- 3
Brunelle DJ.
Macrocycles for the synthesis of high molecular weight polymers. In
New Methods of Polymer Synthesis vol.
2,
JR Ebdon,
GC Eastmond (eds).
Blackie: London,
1995;
197–235.
10.1007/978-94-011-0607-8_6 Google Scholar
- 4 Hodge P. Some applications of reactions which interconvert monomers, polymers and/or macrocycles. React. Funct. Polym. 2001; 48: 15–23.
- 5 Hall AJ, Hodge P. Recent research on the synthesis and applications of cyclic oligomers. React. Funct. Polym. 2001; 48: 133–139.
- 6 Hodge P, Colquhoun HM. Recent work on entropically-driven ring-opening polymerizations: some applications. Polym. Adv. Technol. 2005; 16: 84–94.
- 7 Semlyen JA. Ring-chain equilibriums and the conformations of polymer chains. Adv. Polym. Sci. 1976; 21: 41–75.
- 8
Suter UW.
Ring-chain Equilibria. In
Comprehensive Polymer Science, vol.
5,
G Allen,
JC Bevington (eds).
Pergamon: Oxford,
1989;
91–96.
10.1016/B978-0-08-096701-1.00147-6 Google Scholar
- 9 Ercolani G, Mandolini L, Mencareli P, Roelens S. Macrocyclization under thermodynamic control—A theoretical study and its application to the equilibrium cyclooligomerization of β-propiolactone. J. Am. Chem. Soc. 1993; 115: 3091–3098.
- 10 Brunelle DJ, Shannon TG. Preparation and polymerization of bisphenolA cyclic oligomeric carbonates. Macromolecules 1991; 24: 3035–3044.
- 11 Quihi L, Buese MA. Cyclic carbonates by the depropagation of polycarbonate. Polym. Mater. Sci. Eng. 1992; 67: 457–458.
- 12 Hodge P, Kamau SD. Entropically driven ring-opening metathesis polymerization of macrocyclic olefins with 21–84 ring atoms. Angew. Chem. Int. Ed. Engl. 2003; 42: 2412–2414.
- 13 Hosokawa C, Sakamoto S, Kusomoto T. Organic electroluminescent elements. European Patent 0557 534 A1, (1992).
- 14 Williams RT, Hodge P, Yeates SG. Synthesis of polyesters displaying high fluorescence intensities. React. Funct. Polym. 2007; 67: 1061.
- 15 Kamau SD. Studies on the synthesis, characterization and polymerization of cyclic oligomers. PhD Thesis, University of Manchester, 2003.
- 16 Williams RT. Synthesis of novel polymers for applications in electroluminescent devices. PhD Thesis, University of Manchester, 2001.
- 17 Kamau SD, Hodge P, Williams RT, Stagnaro P, Conzatti L. High throughput synthesis of polyesters using entropically-driven ring-opening polymerizations. (in prep.).
- 18 Brunelle DJ. Macrocycles for the synthesis of high molecular weight polymers. In New Methods of Polymer Synthesis, Vol 2, JR Ebdon, GC Eastmond (eds). Blackie: London, 1995; 220.
- 19 Wilson JW, Burger A, Turnbull LB, Peters M, Milnes F. Unsymmetrical p,p'-disubstituted diphenylhexanes related to hexestrol. J. Org. Chem. 1953; 18: 96–105.
- 20 Tadros W, Akhnookh Y, Aziz Z. Triphenylethylenes and related compounds. J. Chem. Soc. 1953; 107: 186–189.
- 21 Tadros W, Farahat K, Robson JM. Synthetic estrogens related to triphenyl-ethylene. J. Chem. Soc. 1949; 439–441.
- 22 Pommerehne J, Vestweber H, Guss W, Mahrt RF, Bassler H, Porsch M, Daub J. Efficient two layer LEDs on a polymer blend basis. Adv. Mater. 1995; 7: 551–554.
- 23 Muller CD, Falcou A, Reckefuss N, Rojahn M, Wiederhirn V, Rudati P, Frohne H, Nuyken O, Becker H, Meerholz HK. Multi-colour organic light-emitting displays by solution processing. Nature 2003; 421: 829–833.
- 24 Van Woudenbergh T, Wildeman J, Blom PWM. Bias-dependent current efficiency in polymer light-emitting diodes. Semicond. Sci. Technol. 2006; 21: 387–391.
- 25 Friend RH, Gymer RW, Holmes AB, Burroughes JH, Marks RN, Taliani C, Bradley DCC, Dos Santos DA, Bredas JL, Loghlund M, Salaneck WR. Electroluminescence in conjugated polymers. Nature 1999; 397: 121–128.
