Preparation and characterization of novel p-acryloyloxybenzaldehyde copolymers bearing pyrene or fluorescein moieties. Interaction of fluorophore with some quenchers and silver nanoparticles

Designed Monomers and Polymers

Volumn 17, Issue 1, 2014, Pages 89-100

  Buruiana, Emil C ^a   Podasca, Viorica E ^a   Buruiana, Tinca ^a  

^a PETRU PONI INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Romania)

Author keywords

Pyrene fluorescein copolymers; Quenching study; Silver nanoparticles polymer composites

Indexed keywords

FLUORESCENCE PROPERTIES; FLUORESCENCE QUENCHING; QUENCHING EFFICIENCY; QUENCHING STUDIES; RADICAL COPOLYMERIZATION; SILVER NANOPARTICLE (NPS); SILVER NANOPARTICLES; TETRACYANOQUINODIMETHANE;

CHEMICAL MODIFICATION; COPOLYMERS; DIFFERENTIAL SCANNING CALORIMETRY; FILM PREPARATION; FLUORESCENCE; GEL PERMEATION CHROMATOGRAPHY; METAL NANOPARTICLES; PHENOLS; PHOTOPOLYMERS; PYRENE; QUENCHING; THERMOGRAVIMETRIC ANALYSIS;

SILVER;

EID: 84886087846     PISSN: 1385772X     EISSN: 15685551     Source Type: Journal    
DOI: 10.1080/15685551.2013.840512     Document Type: Article

References (45)

1. Moon JH, Yang S. Chemical aspects of 3D photonic crystals. Chem. Rev. 2010;110: 547-574.
2. Yu H, Naka Y, Shishido A, Ikeda T. Well-defined liquid-crystalline diblock copolymers with an azobenzene moiety: synthesis, photoinduced alignment and their holographic properties. Macromolecules. 2008;41: 7959-7966.
3. Angiolini L, Benelli T, Giorgini L, Mauriello F, Salatelli E. Synthesis of optically active photoresponsive multifunctional polymer containing the side-chain azocarbazole chromophore. Macromol. Chem. Phys. 2006;207: 1805-1813.
4. Ito H. Chemical amplifications resists for microlithography. Adv. Polym. Sci. 2005;172: 37-245.
5. Silva AP, Dixon IM, Gunaratne HQN, Gunnlaugsson T, Maxwell PRS, Rice TE. Integration of logic functions and sequential operation of gates at the molecular-scale. J. Am. Chem. Soc. 1999;121: 1393-1394.
6. Connor DM, Kriegel RM, Collard DM, Liotta CL, Schiraldi DA. Pyrene and anthracene dicarboxylic acids as fluorescent brightening comonomers for polyester. J. Polym. Sci., Part A: Polym. Chem. 2000;38: 1291-1301.
7. Gacal BN, Koz B, Gacal B, Kiskan B, Erdogan M, Yagci Y. Pyrene functional poly(vinyl alcohol) by "click" chemistry. J. Polym. Sci., Part A: Polym. Chem. 2009;47: 1317-1326.
8. Pietsch C, Vollrath A, Hoogenboom R, Schubert US. Schubert US. A fluorescent thermometer based on a pyrene- labeled thermoresponsive polymer. Sensors. 2010;10: 7979-7990.
9. Buruiana EC, Podasca V, Buruiana T. Synthesis of block copolymers derived from N-trityl-(S)-serine and pyrene end-labeled poly(methylmethacrylate) or poly(N-isopropylacrylamide) via ATRP. J. Lumin. 2012;132: 2704-2713.
10. Char K, Gast AP, Frank CW. Fluorescence studies of polymer adsorption. 1. Rearrangement and displacement of pyrene-terminated polyethylene glycol on colloidal silica particles. Langmuir. 1988;4: 989-998.
11. Menon S, Das S. Photoresponsive self-assembling structures from a pyrene-based triblock copolymer. J. Polym. Sci., Part A: Polym. Chem. 2011;49: 4448-4457.
12. Mizusaki M, Morishima Y, Winnik FM. Hydrophobically modified poly(sodium 2-acrylamido-2-methylpropanesulfonate) s bearing octadecyl groups: a fluorescence study of their solution properties in water. Macromolecules. 1999;32: 4317-4326.
13. Durmaz H, Dag A, Tunca UG Synthesis and characterization of pyrene bearing amphiphilic miktoarm star polymer and its noncovalent interactions with multiwalled carbon nanotubes. J. Polym. Sci., Part A: Polym. Chem. 2012;50: 2406-2414.
14. Park J, Hammond PT. Polyelectrolyte multilayer formation on neutral hydrophobic surfaces. Macromolecules. 2005;38: 10542-10550.
15. Deo P, Deo N, Somasundaran P, Jockusch S, Turro NJ. Conformational changes of pyrenelabeled polyelectrolytes with pH: effect of hydrophobic modifications. J. Phys. Chem. B. 2005;109: 20714-20718.
16. Chen J, Dong WF, Mohwald H, Ktastev R. Amplified fluorescence quenching of self assembled polyelectrolyte-dye nanoparticles in aqueous solution. Chem. Mater. 2008;20: 1664-1666.
17. Crowley KS, Phillion DP, Woodard SS, Schweitzer BA, Singh M, Shabany H, Burnette B, Hippenmeyer P, Heitmeier M, Bashkin JK. Controlling the intracellular localization of fluorescent polyamide analogues in cultured cells. Bioorg. Med. Chem. Lett. 2003;13: 1565-1570.
18. Lee JK, Heimer BW, Sikes HD. Systematic study of fluorescein- functionalized macrophotoinitiators for colorimetric bioassays. Biomacromolecules. 2012;13: 1136-1143.
19. Fomine S, Pineda A, Ogawa T, Perez R, Sotelo M. Synthesis of polynorbornene containing fluorescein moiety. Polym. J. 1995;27: 1173-1179.
20. Wang B, Guan X, Hu Y, Su Z. Synthesis and photophysical behavior of a water-soluble fluorescein-bearing polymer for Fe3+ ion sensing. J. Polym. Res. 2008;15: 427-433.
21. Wang D, Liu T, Yin J, Liu S. Stimuli-responsive fluorescent poly(N-isopropylacrylamide) microgels labeled with phenylboronic acid moieties as multifunctional ratiometric probes for glucose and temperatures. Macromolecules. 2011;44: 2282-2290.
22. Aoun R, Yassin A, Jamal ME, Kanj A, Berthelot JR, Poriel C. Synthesis of a fluoresceinederivatized fluorene and its electrogenerated copolymers with fluorene: new pH indicators. Synth. Met. 2008;158: 790-795.
23. Zhang Y, Aslan K, Previte MJR, Geddes CD. Metalenhanced excimer (P-type) fluorescence. Chem. Phys. Lett. 2008;458: 147-151.
24. Kang KA, Wang J, Jasinski JB, Achilefu S. Fluorescence manipulation by gold nanoparticles: from complete quenching to extensive enhancement. J. Nanobiotechnol. 2011;9:16.
25. Iosin M, Baldeck P, Astilean S. Plasmon-enhanced fluorescence of dye molecules. Nucl. Instrum. Methods Phys. Res., Sect. B. 2009;267: 403-405.
26. Kudrinskiy AA, Krutyakov YuA, Olenin AYu, Romanovskaya GI, Vasilyeva SYu, Lisichkin GV. Sensitized fluorescence of silver nanoparticles in the presence of pyrene. J. Fluoresc. 2009;19: 473-478.
27. Aslan K, Leonenko Z, Lakowicz JR, Geddes CD. Annealed silver-island films for applications in metalenhanced fluorescence: interpretation in terms of radiating plasmons. J. Fluoresc. 2005;15: 643-654.
28. Chen J, Jin Y, Fahruddin N, Zhao JX. Development of gold nanoparticle-enhanced fluorescent nanocomposites. Langmuir. 2013;29: 1584-1591.
29. Cai X, Anyaogu KC, Neckers DC. Photopolymerization of conductive polymeric metal nanoparticles. Photochem. Photobiol. Sci. 2009;8: 1568-1573.
30. Avella M, Errico ME, Martelli S, Martuscelli E. Preparation methodologies of polymer matrix nanocomposites. Appl. Organomet. Chem. 2001;15: 435-439.
31. Sangermano M, Yagci Y, Rizza G. In situ synthesis of silver-epoxy nanocomposites by photoinduced electron transfer and cationic polymerization processes. Macromolecules. 2007;40: 8827-8829.
32. Yagci Y, Sangermano M, Rizza G. In situ synthesis of goldcross- linked poly(ethylene glycol) nanocomposites by photoinduced electron transfer and free radical polymerization processes. Chem. Commun. 2008;24: 2771-2773.
33. Buruiana EC, Chibac AL, Buruiana T, Melinte V, Balan L. A benzophenone-bearing acid oligodimethacrylate and its application to the preparation of silver/gold nanoparticles/ polymer nanocomposites. J. Nanopart. Res. 2012;15: 1335-1335.
34. Dallas P, Sharma VK, Zboril R. Silver polymeric nanocomposites as advanced antimicrobial agents: classification, synthetic paths, applications, and perspectives. Adv. Colloid Interface Sci. 2011;166: 119-135.
35. Lu HW, Liu SM, Wang XL, Qian XF, Yin J, Zhu ZK. Silver nanocrystals by hyperbranched polyurethaneassisted photochemical reduction of Ag+. Mater. Chem. Phys. 2003;81: 104-107.
36. Sakamoto M, Fujistuka M, Majima T. Light as a construction tool of metal nanoparticles: Synthesis and mechanism. J. Photochem. Photobiol., C. 2009;10: 33-56.
37. Korcheo AS, Bozach MJ, Slaten BL, Mills G. Polymerinitiated photogeneration of silver nanoparticles in SPEEK/PVA films: direct metal photopatterning. J. Am. Chem. Soc. 2004;126: 10-11.
38. Balan L, Jin M, Malval JP, Chaumeil H, Defoin A, Vidal L. Fabrication of silver nanoparticle-embedded polymer promoted by combined photochemical properties of a 2,7-diaminofluorene derivative dye. Macromolecules. 2008;41: 9359-9365.
39. Lindemann MK. Polymer handbook . 4th ed. New York: Wiley; 1999. Chapter V, Physical constants of poly(vinyl acetate); p. 71-76.
40. Winnik FM. Photophysics of preassociated pyrenes in aqueous polymer solutions and in other organized media. Chem. Rev. 1993;93: 587-614.
41. Sjoback R, Nygren J, Kubista M. Characterization of fluorescein- oligonucleotide conjugates and measurement of local electrostatic potential. Biopolymers. 1998;46: 445-453.
42. Munkholm C, Parkinson DR, Walt DR. Intramolecular fluorescence self-quenching of fluoresceinamine. J. Am. Chem. Soc. 1990;112: 2608-2612.
43. Pastoriza-Santos I, Liz-Marzamn LM. Formation and stabilization of silver nanoparticles through reduction by N, N-dimethylformamide. Langmuir. 1999;15: 948-951.
44. Yagci Y, Sahin O, Ozturk T, Marchi S, Grassini S, Sangermano M. Synthesis of silver/epoxy nanocomposites by visible light sensitization using highly conjugated thiophene derivatives. React. Funct. Polym. 2011;71: 857-862.
45. Lin YW, Liu CW, Chang HT. Biodetection based on fluorescence quenching and surfaceenhanced fluorescence using noble metal nanoparticles. In: Chaw LK, Chang HT, editors. From bioimaging to biosensors: noble metal nanoparticles in biodetection. Singapore: Pan Stanford; 2012. p. 211-248.