Formation and characterization of stable fluorescent complexes between neutral conjugated polymers and cyclodextrins

Journal of Fluorescence

Volumn 23, Issue 1, 2013, Pages 171-180

  Martínez Tomé, Maria José ^a   Esquembre, Rocío ^a   Mallavia, Ricardo ^a   Mateo, C Reyes ^a  

^a MIGUEL HERNÁNDEZ UNIVERSITY   (Spain)

Author keywords

Conjugated polymers; Cyclodextrins; Fluorescence; Polyfluorene; Sol gel matrix

Indexed keywords

AQUEOUS MEDIA; CDS; ENVIRONMENTAL APPLICATIONS; HIGH CONCENTRATION; HYBRID MATRIX; NON-POLAR; POLYFLUORENES; POLYMER AGGREGATIONS; POLYMER BACKBONES; SIDE-CHAINS; SOL-GEL MATRIX; SOLUBILISATION; WATER SOLUBILIZATION;

BENZENE; BIOLOGICAL MATERIALS; CONJUGATED POLYMERS; CYCLODEXTRINS; SOL-GEL PROCESS; SOL-GELS; SOLUBILITY; STABILIZATION;

FLUORESCENCE;

CYCLODEXTRIN; FLUORENE DERIVATIVE; FLUORESCENT DYE; POLY (9,9 BIS(6' BROMOHEXYL 2,7 FLUOREN DYIL) CO ALT (BENZENE 1,4 DIY)); POLY-(9,9-BIS(6'-BROMOHEXYL-2,7-FLUOREN-DYIL)-CO-ALT-(BENZENE-1,4-DIY)); POLYMER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION;

CYCLODEXTRINS; FLUORENES; FLUORESCENT DYES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; POLYMERS;

EID: 84873208345     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-012-1130-5     Document Type: Article

References (46)

1. Facchetti A (2011) pi-Conjugated polymers for organic electronics and photovoltaic cell applications. Chem Mater 23:733-758
2. Thomas SW III, Joly GD, Swager TM (2007) Chemical sensors based on amplifying fluorescent conjugated polymers. Chem Rev 107:1339-1386
3. Feng F, Liu L, Wang S (2010) Fluorescent conjugated polymer-based FRET technique for detection of DNA methylation of cancer cells. Nat Protoc 5:1255-1264
4. Gaylord BS, Heeger AJ, Bazan GC (2002) DNA detection using water-soluble conjugated polymers and peptide nucleic acid probes. Proc Natl Acad Sci U S A 99:10954-10957
5. Liu B, Bazan GC (2004) Homogeneous fluorescence-based DNA detection with water-soluble conjugated polymers. Chem Mater 16:4467-4476
6. Duarte A, Pu KY, Liu B, Bazan GC (2011) Recent advances in conjugated polyelectrolytes for emerging optoelectronic applications. Chem Mater 23:501-515
7. Van Den Boogaard M, Bonnet G, Van't Hof P, Wang Y, Brochon C, Van Hutten P, Lapp A, Hadziioannou G (2004) Synthesis of insulated single-chain semiconducting polymers based on polythiophene, polyfluorene, and β-cyclodextrin. Chem Mater 16:4383-4385
8. Burrows HD, Tapia MJ, Fonseca SM, Pradhan S, Scherf U, Silva CL, Pais AACC, Valente AJM, Schilén K, Alfredsson V, Carnerup AM, Tomsic M, Jamnik A (2009) Solubilization of poly{1,4-phenylene-[9,9-bis(4-phenoxy- butylsulfonate)] fluorene-2,7-diyl} in water by nonionic amphiphiles. Langmuir 25:5545-5556
9. Mallakpour S, Dinari M (2010) A study of the ionic liquid mediated microwave heating for the synthesis of new thermally stable and optically active aromatic polyamides under green procedure. Macromol Res 18:129-136
10. Huang F, Wang X, Wang D, Yang W, Cao Y (2005) Synthesis and properties of a novel water-soluble anionic polyfluorenes for highly sensitive biosensors. Polymer 46:12010-12015
11. Mallavia R, Martinez-Perez D, Chmelka BF, Bazan GC (2004) Blue fluorescent films based on poly-2,7-fluorene-phenylene derivatives. Bol Soc Esp Ceram V 43:327-330
12. Liu B, Gaylord BS, Wang S, Bazan GC (2003) Effect of chromophore-charge distance on the energy transfer properties of water-soluble conjugated oligomers. J Am Chem Soc 125:6705-6714
13. 2+-mediated carbohydrate-carbohydrate interaction. Biomacromolecules 11:13-19
14. Burrows HD, Lobo VMM, Pina J, Ramos ML, De Seixas Melo J, Valente AJM, Tapia MJ, Pradhan S, Scherf U (2004) Fluorescence enhancement of the water-soluble poly{1,4-phenylene-[9,9-bis- (4-phenoxybutylsulfonate)]fluorene-2, 7-diyl} copolymer in n- dodecylpentaoxyethylene glycol ether micelles. Macromolecules 37:7425-7427
15. Jiang H, Taranekar P, Reynolds JR, Schanze KS (2009) Conjugated polyelectrolytes: synthesis, photophysics, and applications. Angew Chem Int Ed 48:4300-4316
16. Burnell T, Cella JA, Donahue P, Duggal A, Early T, Heller CM, Liu J, Shiang J, Simon D, Slowinska K, Sze M, Williams E (2005) Synthesis and electrooptical properties of copolymers derived from phenol-functionalized telechelic oligofluorenes. Macromolecules 38:10667-10677
17. Wang ZY, Hay AS (1991) Synthesis of poly(arylene ether)s based on 9,9-bis(3,5-diphenyl-4-hydroxyphenyl)fluorene. J Polymer Sci Polymer Chem 29:1045-1052
18. Zhou XH, Yan JC, Pei J (2004) Exploiting an imidazole-functionalized polyfluorene derivative as a chemosensory material. Macromolecules 37:7078-7080
19. Zhou G, Qian G, Ma L, Cheng Y, Xie Z, Wang L, Jing X, Wang F (2005) Polyfluorenes with phosphonate groups in the side chains as chemosensors and electroluminescent materials. Macromolecules 38:5416-5424
20. Xue C, Donuru VRR, Liu H (2006) Facile, versatile prepolymerization and postpolymerization functionalization approaches for well-defined fluorescent conjugated fluorene-based glycopolymers. Macromolecules 39:5747-5752
21. Tapia MJ, Montserín M, Valente AJ, Burrows HD, Mallavia R (2010) Binding of polynucleotides to conjugated polyelectrolytes and its applications in sensing. Adv Colloid Interface Sci 158:94-107
22. Martínez-Tomé MJ, Esquembre R, Mallavia R, Mateo CR (2010) Formation of complexes between the conjugated polyelectrolyte poly{[9,9-bis(6′-n, n, ntrimethylammonium) hexyl]fluorene-phenylene} bromide (HTMA-PFP) and human serum albumin. Biomacromolecules 11:1494-1501
23. Evans RC, Macedo AG, Pradhan S, Scherf U, Carlos LD, Burrows HD (2010) Fluorene based conjugated polyelectrolyte/silica nanocomposites: charge-mediated phase aggregation at the organic-inorganic interface. Adv Mater 22:3032-3037
24. Grigoras M, Stafie L (2010) Electrically insulated molecular wires. Supramol Chem 22:237-248
25. Huang F, Gibson HW (2005) Polypseudorotaxanes and polyrotaxanes. Prog Polym Sci 30:982-1018
26. Loethen S, Kim JM, Thompson DH (2007) Biomedical applications of cyclodextrin based polyrotaxanes. Polym Rev 47:383-418
27. Harada A, Takashima Y, Yamaguchi H (2009) Cyclodextrin-based supramolecular polymers. Chem Soc Rev 38:875-882
28. El-Kemary MA, El-Mehasseb IM (2004) Global and distribution analysis of fluorescence decays and spectrofluorimetric determination of stoichiometry and association constant of the inclusion complex of 2-amino-5,6-dimethyl- benzimidazole with β-cyclodextrin. Talanta 62:317-322
29. Gazpio C, Sánchez M, Zornoza A, Martín C, Martínez-Ohárriz C, Vélaz I (2003) A fluorimetric study of pindolol and its complexes with cyclodextrins. Talanta 60:477-482
30. Manzoori JL, Amjadi M (2003) Spectrofluorimetric study of host-guest complexation of ibuprofen with β-cyclodextrin and its analytical application. Spectrochim Acta Part A 59:909-916
31. Michels JJ, O'Connell MJ, Taylor PN, Wilson JS, Cacialli F, Anderson HL (2003) Synthesis of conjugated polyrotaxanes. Chem Eur J 9:6167-6176
32. Cacialli F, Wilson JS, Michels JJ, Daniel C, Silva C, Friend RH, Severin N, Samori P, Rabe JP, O'Connell MJ, Taylor PN, Anderson HL (2002) Cyclodextrin-threaded conjugated polyrotaxanes as insulated molecular wires with reduced interstrand interactions. Nat Mater 1:160-164
33. Farcas A, Jarroux N, Harabagiu V, Guégan P (2009) Synthesis and characterization of a poly[2,7-(9,9-dioctylfluorene-alt-2,7-fluorene/ β-CD)] main chain polyrotaxane. Eur Polym J 45:795-803
34. Farcas A, Ghosh I, Jarroux N, Harabagiu V, Guégan P, Nau WM (2008) Morphology and properties of a polyrotaxane based on γ-cyclodextrin and a polyfluorene copolymer. Chem Phys Lett 465:96-101
35. Jung Y, Hickey RJ, Park SJ (2010) Encapsulating light-emitting polymers in block copolymer micelles. Langmuir 26:7540-7543
36. Mallavia R, Montilla F, Pastor I, Velásquez P, Arredondo B, Álvarez AL, Mateo CR (2005) Characterization and side chain manipulation in violet-blue poly-[(9,9-dialkylfluoren-2,7-diyl)-alt-co-(benzen-1,4-diyl)] backbones. Macromolecules 38:3185-3192
37. Molina R, Gómez-Ruiz S, Montilla F, Salinas-Castillo A, Fernández-Arroyo S, Del Mar Ramos M, Micol V, Mallavia R (2009) Progress in the synthesis of poly(2,7-fluorene-alt-1,4-phenylene), PFP, via suzuki coupling. Macromol 42:5471-5477
38. Benesi HA, Hildebrand JH (1949) A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 71:2703-2707
39. Wenz G, Han BH, Müller A (2006) Cyclodextrin rotaxanes and polyrotaxanes. Chem Rev 106:782-817
40. van de Manakker F, Vermonden T, van Nostrum CF, Hennink WE (2009) Cyclodextrin-based polymeric materials: synthesis, properties, and pharmaceutical/biomedical applications. Biomacromolecules 10:3157-3175
41. He Y, Fu P, Shen X, Gao H (2008) Cyclodextrin-based aggregates and characterization by microscopy. Micron 39:495-516
42. Loftsson T, Másson M, Brewster ME (2004) Self-association of cyclodextrins and cyclodextrin complexes. J Pharm Sci 93:1091-1099
43. Traiphol R, Sanguansat P, Srikhirin T, Kerdcharoen T, Osotchan T (2006) Spectroscopic study of photophysical change in collapsed coils of conjugated polymers: effects of solvent and temperature. Macromolecules 39:1165-1172
44. Esquembre R, Poveda JA, Mateo CR (2009) Biophysical and functional characterization of an Ion channel peptide confined in a Sol-gel matrix. J Phys Chem B 113:7534-7540
45. Livage J, Coradin T, Roux C (2001) Encapsulation of biomolecules in silica gels. J Phys Condens Matter 13:R673-R691
46. Pastor I, Ferrer ML, Lillo MP, Gómez J, Mateo CR (2007) Structure and dynamics of lysozyme encapsulated in a silica sol-gel matrix. J Phys Chem B 111:11603-11610