A Pyrene- and Phosphonate-Containing Fluorescent Probe as Guest Molecule in a Host Polymer Matrix
Abstract
:1. Introduction
2. Results and Discussion
2.1. Characteristics of the Host and Guest Species
2.2. Insertion of CCNPyr in Copo C6-H Polymeric Matrix
2.3. Insertion of Pyrene (Pyr) in Copo C6-H Polymeric Matrix
2.4. Insertion of N-Pyrenylmaleimide (NPyrMal) in Copo C6-H Polymeric Matrix
2.5. Insertion of CCNPyr in Polyethylene glycol (PEG-5000)
3. Experimental
3.1. Materials
3.2. Analytical Methods
3.3. Synthesis of Pyrene-Containing Fluorescence Diethyl (1,1a,3,3a,4,7)-hexahydro-1,3-dioxo-2-(pyren-1-yl)-2H-isoindol-4-phosphonate-1,3-dione (CCNPyr, Figure 2)
3.4. General Procedure for the Preparation of “Host-Guest” Materials
4. Conclusions
Supplementary Materials
Acknowledgments
References
- Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; Wiley-VCH: Weinheim, Germany, 1995; p. 271. [Google Scholar]
- Camacho, C.; Matías, J.C.; Cao, R.; Matos, M.; Chico, B.; Hernández, J.; Longo, M.A.; Sanromán, M.A.; Villalonga, R. Hydrogen peroxide biosensor with a supramolecular Layer-by-Layer design. Langmuir 2008, 24, 7654–7657. [Google Scholar] [CrossRef] [PubMed]
- Tung, C.-H.; Wu, L.-Z.; Zhang, L.-P.; Chen, B. Supramolecular systems as microreactors: Control of product selectivity in organic phototransformation. Acc. Chem. Res. 2003, 36, 39–47. [Google Scholar] [CrossRef] [PubMed]
- Schrader, T. Chelate complexes with the P=O double bond- a new concept for molecular recognition. J. Inclusion Phen. Macrocyclic Chem. 1999, 34, 117–129. [Google Scholar]
- Consiglio, G.P.; Failla, S.; Finocchiaro, P. New cleft-like molecules and macrocycles from phosphonate substituted spirobisindanol. Molecules 2008, 13, 678–700. [Google Scholar] [CrossRef] [PubMed]
- Abbel, R.; Grenier, C.; Pouderoijen, M.J.; Stouwdam, J.W.; Leclère, P.E.L.G.; Sijbesma, R.P.; Meijer, E.W.; Schenning, A.P.H.J. White-light emitting hydrogen-bonded supramolecular copolymers based on π–conjugated oligomers. J. Am. Chem. Soc. 2009, 131, 833–843. [Google Scholar] [CrossRef] [PubMed]
- Kulikovska, O.; Goldenberg, L.M.; Stumpe, J. Supramolecular azobenzene-based materials for optical generation of microstructures. Chem. Mat. 2007, 19, 3343–3348. [Google Scholar] [CrossRef]
- Bernhardt, S.; Kastler, M.; Enkelmann, V.; Baumgarten, M.; Müllen, K. Pyrene as chromophore and electrophore: Encapsulation in a rigid polyphenylene shell. Chem. Eur. J. 2006, 12, 6117–6128. [Google Scholar] [CrossRef] [PubMed]
- Kalyanasundaram, K.; Thomas, J.K. Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems. J. Am. Chem. Soc. 1977, 99, 2039–2044. [Google Scholar] [CrossRef]
- Dong, D.C.; Winnik, M.A. The Py scale of solvent polarities. Can. J. Chem. 1984, 62, 2560–2565. [Google Scholar] [CrossRef]
- Bains, G.; Patel, A.B.; Narayanaswami, V. Pyrene: A probe to study protein conformation and conformational changes. Molecules 2011, 16, 7909–7935. [Google Scholar] [CrossRef] [PubMed]
- Yang, M.-H.; Thirupathi, P.; Lee, K.-H. Selective and sensitive ratiometric detection of Hg(II) ions using a simple amino acid based sensor. Org. Lett. 2011, 13, 19, 5028–5031. [Google Scholar] [CrossRef] [PubMed]
- Jung, H.S.; Park, M.; Han, D.Y.; Kim, E.; Lee, C.; Ham, S.; Kim, J.S. Cu2+ Ion-induced self-assembly of pyrenylquinoline with a pyrenyl excimer formation. Org. Lett. 2009, 11, 3378–3381. [Google Scholar] [CrossRef] [PubMed]
- Nishimura, Y.; Takemura, T.; Arai, S. Li+ selective podand-type fluoroionophore based on a diphenyl sulfoxide derivative bearing two pyrene groups. Molecules 2011, 16, 6844–6857. [Google Scholar] [CrossRef] [PubMed]
- Huang, J.; Wu, Y.; Chen, Y.; Zhu, Z.; Yang, X.; Yang, C.J.; Wang, K.; Tan, W. Pyrene-excimer probes based on the hybridization chain reaction for the detection of nucleic acids in complex biological fluids. Angew. Chem. Int. Ed. 2011, 50, 401–404. [Google Scholar] [CrossRef] [PubMed]
- Masuko, M.; Ohtani, H.; Ebata, K.; Shimadzu, A. Optimization of excimer-forming two probe nucleic acid hybridization method with pyrene as a fluorophore. Nucleic Acids Res. 1998, 26, 5409–5416. [Google Scholar] [CrossRef] [PubMed]
- Duhamel, J. New Insights in the Study of Pyrene Excimer fluorescence to characterize Macromolecules and their supramolecular assemblies in solution. Langmuir 2012, 28, 6527–6538. [Google Scholar] [CrossRef] [PubMed]
- Cicchi, S.; Fabbrizzi, P.; Ghini, G.; Brandi, A.; Foggi, P.; Marcelli, A.; Righini, R.; Botta, C. Pyrene-excimers-based antenna systems. Chem. Eur. J. 2009, 15, 754–764. [Google Scholar] [CrossRef] [PubMed]
- Szadkowska-Nicze, M.; Wolszczak, M.; Kroh, J.; Mayer, J. Concentration dependence of pyrene excimer formation in doped polyethylene. J. Photochem. Photobiol. A: Chem. 1993, 75, 125–129. [Google Scholar] [CrossRef]
- Hrdlovič, P.; Chmela, Š. Spectral characteristics of multifunctional probes based on pyrene in solution and in polymer matrices. J. Photochem. Photobiol. A: Chem. 1997, 105, 83–88. [Google Scholar] [CrossRef]
- Pujari, S.R.; Kambale, M.D.; Bhosale, P.N.; Rao, P.M.R.; Patil, S.R. Optical properties of pyrene doped polymer thin films. Mat. Res. Bull. 2002, 37, 1641–1649. [Google Scholar] [CrossRef]
- Johnson, G.E. Effect of Concentration on the fluorescence spectra and lifetimes of pyrene in polystyrene films. Macromolecules 1980, 13, 839–844. [Google Scholar] [CrossRef]
- Hrdlovič, P.; Chmela, Š. Spectral characteristics of probes based on ionic derivatives of pyrene in polar polymer matrices. J. Photochem. Photobiol. A: Chem. 1998, 118, 137–142. [Google Scholar] [CrossRef]
- Avis, A.; Porter, G. Effect of Concentration on the absorption and fluorescence spectra of pyrene in a solid solution of poly(methyl methacrylate). J. Chem. Soc. Faraday Trans. II 1974, 70, 1057–1065. [Google Scholar] [CrossRef]
- Danko, M.; Hrdlovič, P.; Borsig, E. Quenching of pyrene fluorescence as a technique for characterisation of swelling of interpenetrating polymer network: Polyethylene/Poly(styrene-co-butylmethacrylate). Eur. Poly. J. 2003, 39, 2175–2182. [Google Scholar] [CrossRef]
- Zeng, L.; Wu, J.; Dai, Q.; Liu, W.; Wang, P.; Lee, C.-S. Sensing of bacterial endotoxin in aqueous solution by supramolecular assembly of pyrene derivative. Org. Lett. 2010, 12, 4014–4017. [Google Scholar] [CrossRef] [PubMed]
- Dai, Q.; Liu, W.; Zhuang, X.; Wu, J.; Zhang, H.; Wang, P. Ratiometric fluorescence sensor based on a pyrene derivative and quantification detection of heparin in aqueous solution and serum. Anal. Chem. 2011, 83, 6559–6564. [Google Scholar] [CrossRef] [PubMed]
- Ramos, A.S.F.; Techert, S. A directly linked pyrene–dimethylaniline derivative as a potential biochemical sensor for the microenvironmental dielectric properties of the active site of enzymes. Phys. Chem. Chem. Phys. 2003, 5, 5176–5181. [Google Scholar] [CrossRef]
- Backes, C.; Mundloch, U.; Ebel, A.; Haucke, F.; Hirsch, A. Dispersion of HiPco® and CoMoCAT® Single-Walled Nanotubes (SWNTs) by water soluble pyrene derivatives-depletion of small diameter SWNTs. Chem. Eur. J. 2010, 16, 3314–3317. [Google Scholar] [CrossRef] [PubMed]
- Yip, H.-L.; Ma, H.; Jen, A.K.-Y.; Dong, J.; Parviz, B.A. Two-dimensional self-assembly of 1-Pyrylphosphonic acid: Transfer of stacks on structurated surface. J. Am. Chem. Soc. 2006, 128, 5672–5679. [Google Scholar] [CrossRef] [PubMed]
- Villemin, E.; Elias, B.; Robiette, R.; Robeyns, K.; Herent, M.-F.; Habib-Jiwan, J.-L.; Marchand-Brynaert, J. Novel phosphonated bicyclic frameworks from diels–alder reaction as chelating agents of di- and trivalent metal cations. Tetrahedron Lett. 2011, 52, 5140–5144. [Google Scholar] [CrossRef]
- Villemin, E.; Robeyns, K.; Robiette, R.; Herent, M.-F.; Marchand-Brynaert, J. Polycyclic phosphonic acid derivatives obtained by a [4+2] cycloaddition strategy using phosphonodienes. Tetrahedron 2013, 69, 1138–1147. [Google Scholar] [CrossRef]
- Villemin, E.; Herent, M.-F.; Marchand-Brynaert, J. Functionalized phosphonated half-cage molecules as ligands for metal complexes. Eur. J. Org. Chem. 2012, 31, 6165–6178. [Google Scholar] [CrossRef]
- Rullens, F.; Devillers, M.; Laschewsky, A. New regular, amphiphilic poly(ampholyte)s: Synthesis and characterization. Macromol. Chem. Phys. 2004, 205, 1155–1166. [Google Scholar] [CrossRef]
- Deligne, N.; Bayot, D.; Degand, M.; Devillers, M. Nb-Ta, Nb-Mo and Nb-V oxides prepared from hybrid organic-inorganic precursors. J. Solid State Chem. 2007, 180, 2026–2033. [Google Scholar] [CrossRef]
- Rullens, F.; Devillers, M.; Laschewsky, A. Preparation of simple and mixed nickel and cobalt molybdates using hybrid precursors made from an ordered polymer matrix and inorganic salts. J. Mater. Chem. 2004, 14, 3421–3426. [Google Scholar] [CrossRef]
- Takahashi, K. Organic reactions mediated by cyclodextrins. Chem. Rev 1998, 98, 2013–2034. [Google Scholar] [CrossRef] [PubMed]
- Shi, Y.; Wang, D.; Zhang, Z. Fluorescence enhancement of guests by the formation of inclusion complexes with P-Tert-Butylcalix[8]Arene bearing polyoxyethylene chains in aqueous solution. J. Photochem. Photobiol. A Chem. 1995, 91, 3, 211–215. [Google Scholar] [CrossRef]
- Niwayama, S.; Kassar, A.S.; Zhao, T.; Sutton, R.B.; Altenberg, G.A. A pyrene maleimide with a flexible linker for sampling of longer inter-thiol distances by excimer formation. PLoS One 2011, 6, e26691. [Google Scholar] [CrossRef] [PubMed]
- Hofkens, J.; Hotta, K.; Sasaki, K.; Masuhara, H.; Taniguchi, T.; Miyashita, T. Molecular association by the radiation pressure of a focused laser beam: Fluorescence characterization of pyrene-labeled PNIPAM. J. Am. Chem. Soc. 1997, 119, 2741–2742. [Google Scholar] [CrossRef]
- Kokado, K.; Iwamura, T.; Chujo, Y. Synthesis and photoluminescnce properties of pyrne-incorporated organic-inorganic polymer hybrids. Polymer J. 2008, 40, 402–408. [Google Scholar] [CrossRef]
- Deepak, V.D.; Asha, S.K. Photophysical Investigation into the self-organization in pyrene-based urethane methacrylate comb polymer. J. Phys. Chem. B 2009, 113, 11887–11897. [Google Scholar] [CrossRef] [PubMed]
- Lianos, P.; Viriot, M.-L.; Zana, R. Study of the solubilization of aromatic hydrocarbons by aqueous micellar solutions. J. Phys. Chem. 1984, 88, 1098–1101. [Google Scholar] [CrossRef]
- Turro, N.J.; Kuo, P.-L. Pyrene excimer formation in micelles of nonionic detergents and of water-soluble polymers. Langmuir 1986, 2, 438–442. [Google Scholar] [CrossRef]
- Mizusaki, M.; Yusa, S.-I.; Kawanishi, S.; Morishima, Y. Interaction of a pyrene-labeled cholesterol-bearing polyanion with surfactant micelles studied by fluorescence quenching. Polymer 2002, 43, 5865–5871. [Google Scholar] [CrossRef]
- Aricha, B.; Fishov, I.; Cohen, Z.; Sikron, N.; Pesakhov, S.; Khozin-Goldberg, I.; Dagan, R.D.; Porat, N. Differences in membrane fluidity and fatty acid composition between phenotypic variants of Streptococcus pneumoniae. J. Bacteriol. 2004, 186, 14, 4638–4644. [Google Scholar] [CrossRef] [PubMed]
- Thomas, J.L.; Borden, K.A.; Tirell, D.A. Modulation of mobilities of fluorescent membrane probes by adsorption of a hydrophobic polyelectrolyte. Macromolecules 1996, 29, 2570–2576. [Google Scholar] [CrossRef]
- Mohanambe, L.; Vasudevan, S. Aromatic molecules in restricted geometries:pyrene excimer formation in an anchored bilayer. J. Phys. Chem. B 2006, 110, 14345–14354. [Google Scholar] [CrossRef] [PubMed]
- Crawford, A.G.; Dwyer, A.D.; Liu, Z.; Steffen, A.; Beeby, A.; Pålsson, L.-O.; Tozer, D.J.; Marder, T.B. Experimental and theoretical studies of the photophysical properties of 2- and 2,7-functionalized pyrene derivatives. J. Am. Chem. Soc. 2011, 133, 13349–13362. [Google Scholar] [CrossRef] [PubMed]
- Modro, A.M.; Modro, T.A. The phosphoryl and the carbonyl group as hydrogen bond acceptors. Can. J. Chem. 1999, 77, 890–894. [Google Scholar] [CrossRef]
- Ham, F.S. Vibronic model for the relaxed excited state of the f center. I. General solution. Phys. Rev. B 1973, 8, 2926–2944. [Google Scholar] [CrossRef]
- Zhang, Q.; Li, W.; Wang, J.; Zhang, S. Synthesis of isomeric Bis(amine anhydride)s for novel Poly(amine imide)s by Pd-Catalyzed amination of 4-Chlorophthalic anhydride. Polymer 2008, 49, 1191–1198. [Google Scholar] [CrossRef]
- ElMiloudi, K.; Benygzer, M.; Djadoum, S.; Sbirrazzuoli, N.; Geribaldi, S. FT-IR Spectroscopy and hydrogen bondinginteractions in Poly(styrene-co-methacrylic acid)/Poly(styrene-co-4-vinyl pyridine) blends. Macromol. Symp. 2005, 230, 39–50. [Google Scholar] [CrossRef]
- Nyquist, R.A.; Fieder, S.L. Infrared study of five- and six-membered type cyclic imides. Vib. Spectr. 1995, 8, 365–386. [Google Scholar] [CrossRef]
- Mishra, A.K.; Chattopadhyay, D.K.; Sreedhan, B.; Raju, K.V.S.N. FT-IR AND XPS STUDIES OF POLYURETHANE-UREA-IMIDE COATINGS. Prog. Org. Coat. 2006, 55, 231–243. [Google Scholar] [CrossRef]
- Hsu, S.-C.; Whang, W.-T.; Hung, C.-H.; Chiang, P.-C.; Hsiao, Y.-N. Effect of the polyimide structure and ZnO concentration on the morphology and characteristics of Polyimide/ZnO nanohybrid film. Macromol. Chem. Phys. 2005, 206, 291–298. [Google Scholar] [CrossRef]
- Weltman, J.K.; Szaro, R.P.; Frackelton, A.R., Jr.; Dowben, R.M.; Bunting, J.R.; Cathou, R.E. N-(3-Pyrene)maleimide: A long lifetime fluorescent sulfhydryl reagent. J. Biol. Chem. 1973, 248, 3173–3177. [Google Scholar] [PubMed]
- Haque, Md. E.; Ray, S.; Chakrabarti, A. Polarity estimate of the hydrophobic binding sites in erythroid spectrin: A study by pyrene fluorescence. J. Fluoresc. 2000, 10, 1–6. [Google Scholar] [CrossRef]
- Panda, D.; Bhattacharyya, B. Excimer fluorescent of pyren-maleimide-labeled tubulin. Eur. J. Biochem. 1992, 204, 783–787. [Google Scholar] [CrossRef] [PubMed]
- Winters, R.A.; Zukowski, J.; Ercal, N.; Matthews, R.H.; Spitz, D.R. Analysis of glutathione, glutathione disulfide, cysteine, homocysteine, and other biological thiols by high-performance liquid chromatography following derivatization by N-(1-Pyrenyl)maleimide. Anal. Biochem. 1995, 227, 14–21. [Google Scholar] [CrossRef] [PubMed]
- Yukawa, S.; Omayu, A.; Matsumoto, A. Thermally stable fluorescent maleimide/isobutene alternating copolymers containing pyrenyl and alkynylpyrenyl moieties in the side chain. Macromol. Chem. Phys. 2009, 210, 1776–1784. [Google Scholar] [CrossRef]
- Frahn, M.S.; Warman, J.M.; Abellon, R.D.; Luthjens, L.H. Monitoring the radiation-induced bulk polymerization of methyl methacrylate with N-(1-pyrene)maleimide. Radiat. Phys. Chem. 2001, 60, 433–437. [Google Scholar] [CrossRef]
- Shown, I.; Ujihara, M.; Imae, T. Sensitizing of Pyrene Fluorescence by β-Cyclodextrin-Modified TiO2 Nanoparticules. J. Colloid Interface Sci. 2010, 352, 232–237. [Google Scholar] [CrossRef] [PubMed]
Sample Availability: Not available. |
Entry | Material | I/II | I/III | I/V |
---|---|---|---|---|
1 | CCNPyr in cyclohexane | / | 1.49 | 1.15 |
2 | CCNPyr in acetonitrile | / | 2.31 | 1.34 |
3 | Copo C6-H/CCNPyr | / | 0.58 | 0.22 |
4 | Copo C6-H/Pyr (≤0.25 equiv.) | 1.55 | 0.81 | 0.25 |
5 | Copo C6-H/NPyrMal (≤0.25 equiv.) | / | 1.69 | 0.85 |
Guest loading (equiv.) | m CCNPyr (mg) | % wt | m Pyr (mg) | % wt | m NPyrMal (mg) | % wt | m CCNPyr (mg) | % wt |
---|---|---|---|---|---|---|---|---|
for 200 mg of Copo C6-H | for 200 mg of PEG-5000 | |||||||
0.03 | / | / | / | / | / | / | 66.4 | 24.9 |
0.05 | 16.4 | 7.6 | 6.7 | 3.2 | 9.9 | 4.7 | 110.7 | 35.6 |
0.08 | / | / | / | / | 15.9 | 7.4 | / | / |
0.10 | 32.8 | 14.1 | 13.3 | 6.2 | 19.9 | 9.0 | 221.3 | 52.5 |
0.12 | / | / | / | 7.4 | / | / | / | / |
0.25 | 81.9 | 29.1 | 33.3 | 14.3 | 49.7 | 19.9 | / | / |
0.50 or 0.51 | 163.8 | 45.0 | 68.0 | 25.4 | 99.3 | 33.2 | / | / |
© 2013 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
Share and Cite
Villemin, E.; Elias, B.; Devillers, M.; Marchand-Brynaert, J. A Pyrene- and Phosphonate-Containing Fluorescent Probe as Guest Molecule in a Host Polymer Matrix. Molecules 2013, 18, 1897-1915. https://doi.org/10.3390/molecules18021897
Villemin E, Elias B, Devillers M, Marchand-Brynaert J. A Pyrene- and Phosphonate-Containing Fluorescent Probe as Guest Molecule in a Host Polymer Matrix. Molecules. 2013; 18(2):1897-1915. https://doi.org/10.3390/molecules18021897
Chicago/Turabian StyleVillemin, Elise, Benjamin Elias, Michel Devillers, and Jacqueline Marchand-Brynaert. 2013. "A Pyrene- and Phosphonate-Containing Fluorescent Probe as Guest Molecule in a Host Polymer Matrix" Molecules 18, no. 2: 1897-1915. https://doi.org/10.3390/molecules18021897