Synthesis and photophysical properties of poly(arylene ethynylene) small-molecules and polymers derivatized with leucine substituents

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 298, Issue , 2015, Pages 1-8

  Ricci, Antonella ^a   Chiarini, Marco ^a   Lo Sterzo, Claudio ^a   Pizzoferrato, Roberto ^b   Paoloni, Stefano ^b  

^a UNIVERSITY OF TERAMO   (Italy)

^b UNIVERSITY OF ROME TOR VERGATA   (Italy)

Author keywords

Aminoacid; Fluorescence; Poly(arylene ethynylene); Stille coupling

Indexed keywords

EID: 84908389438     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2014.10.003     Document Type: Article

References (39)

1. Handbook of Conducting Polymers T.A. Skotheim, and J. Reynolds 3rd ed. 2007 CRC Press, Taylor & Francis Group Boca Raton
2. A.C. Grimsdale, K.L. Chan, R.E. Martin, P.G. Jokisz, and A.B. Holmes Synthesis of Light-Emitting Conjugated Polymers for Applications in Electroluminescent Devices Chemical Reviews 2009 897 1091 10.1021/cr000013v
3. C.A. Traina, R.C. Bakus II, and G.C. Bazan Design and Synthesis of Monofunctionalized, Water-Soluble Conjugated Polymers for Biosensing and Imaging Applications Journal of the American Chemical Society 2011 12600 12607 10.1021/ja202877q
4. G.M. Farinola, F. Babudri, A. Cardone, O.H. Omar, and F. Naso Synthesis of substituted conjugated polymers: Tuning properties by functionalization Pure and Applied Chemistry 80 2008 1735 1746 10.1351/pac200880081735
5. J.H. Wosnick, C.M. Mello, and T.M. Swager Synthesis and Application of Poly(phenylene Ethynylene)s for Bioconjugation: A Conjugated Polymer-Based Fluorogenic Probe for Proteases Journal of the American Chemical Society 127 2005 3400 3405 10.1021/ja043134b
6. A.K. Shaytan, E.K. Schillinger, E. Mena-Osteritz, S. Schmid, P.G. Khalatur, P. Bauerle, and A.R. Khokhlov Self-organizing bioinspired oligothiophene-oligopeptide hybrids Beilstein J. Nanotechnol. 2 2011 525 544 10.3762/bjnano.2.57
7. B. Jung, and P. Theato Chemical Strategies for the Synthesisof Protein-Polymer Conjugates Advances in Polymer Science 253 2013 37 70 10.1007/12-2012-169
8. A. Aslund, K.P.R. Nilsson, and P. Konradsson Fluorescent oligo and poly-thiophenes and their utilization for recording biological events of diverse origin - when organic chemistry meets biology, J Chemistry and Biology 2 2009 161 175 10.1007/s12154-009-0024-8
9. C. Weder Poly(arylene ethynylene)s - from synthesis to applications Advances in Polymer Science 177 2005 Springer Heidelberg
10. S.W. Thomas III, G.D. Joly, and T.M. Swager Chemical Sensors Based on Amplifying Fluorescent Conjugated Polymers Chemical Reviews 107 2007 1339 1386
11. J.-M. Koenen, X. Zhu, Z. Pan, F. Feng, J. Yang, and K.S. Schanze Enhanced Fluorescence Properties of Poly(phenylene ethynylene)-Conjugated Polyelectrolytes Designed to Avoid Aggregation ACS Macro Lett. 3 2014 405 409
12. V. Farina, V. Krishnammurthy, and W.J. Scott The Stille Reaction 1998 Wiley New York
13. D. Compagnone, A. Ricci, M. Del Carlo, M. Chiarini, A. Pepe, and C. Lo Sterzo New poly(aryleneethynylene)s as optical active platforms in biosensing. Selective fluorescent detection of Hg(II) obtained by the use of aminoacidic groups ancore on conjugated backbones Microchimica Acta 170 2010 313 319 10.1007/s00604-010-0322-4
14. A. Ricci, M. Chiarini, M.T. Apicella, D. Compagnone, M. Del Carlo, C. Lo Sterzo, L. Prodi, S. Bonacchi, D. Villamaina, and N. Zaccheroni Aminoacidic units wired on poly(aryleneethynylene) platforms as highly selective mercury-responsive materials Tetrahedron Letters 54 2013 303 307 10.1016/j.tetlet.2012.11.034
15. 2+ Chemosensor with High Solubility and High Photoluminescence Quantum Yield Macromolecules 42 2009 5427 5429 10.1021/ma9009998
16. C.L. Chochos, and S.A. Choulis How the structural deviations on the backbone of conjugated polymers influence their optoelectronic properties and photovoltaic performance Progress in Polymer Science 36 2011 1326 1414 10.1016/j.progpolymsci.2011.04.003
17. M. Bochmann, and K. Kelly Palladium catalysed cross-coupling reactions with difunctional tin reagents: a general route to aromatic polymers J. Chem. Soc Chemical Communications 1989 532 534 10.1039/C39890000532
18. n, Opto- and Electro-Responsive Materials for Advanced Technology Advanced Synthesis and Catalysis 347 2005 143 160 10.1002/adsc.200404233
19. U.F.H. Bunz Poly(aryleneethynylene)s: syntheses, Properties, Structures, and Applications Chemical Reviews 100 2000 1605 1644 10.1021/cr990257j
20. R. Pizzoferrato, M. Berliocchi, A. Di Carlo, M. Venanzi, A. Micozzi, A. Ricci, and C. Lo Sterzo Improvement of the Extended One-Pot (EOP) Procedure To Form Poly(aryleneethynylene)s and Investigation of Their Electrical and Optical Properties Macromolecules 36 2003 2215 2223 10.1021/ma0216829
21. A. Beeby, K. Findlay, and P.J.T.B. Low Marder A Re-evaluation of the Photophysical Properties of 1,4-Bis(phenylethynyl) benzene: A Model for Poly(phenyleneethynylene) Journal of the American Chemical Society 124 2002 8280 8284 10.1021/ja025568h
22. M. Biswas, P. Nguyen, T.B. Marder, and L.R. Khundkar Unusual Size Dependence of Nonradiative Charge Recombination Rates in Acetylene-Bridged Compounds J. Phys. Chem. A 101 1997 1689 1695 10.1021/jp960851
23. S. Kumar Spectroscopic studies of valine and leucine molecules a comparative study Elixir Vib. Spec. 39 2011 4996 4999
24. J.-M. Koenen, X. Zhu, Z. Pan, F. Feng, J. Yang, and K.S. Schanze Enhanced Fluorescence Properties of Poly(phenylene ethynylene)-Conjugated Polyelectrolytes Designed to Avoid Aggregation ACS Macro Lett. 3 2014 405 409 10.1021/mz500067k
25. S.H. Lee, S. Komurlu, X. Zhao, H. Jiang, G. Moriena, V.D. Kleiman, and K.S. Schanze Water-Soluble Conjugated Polyelectrolytes with Branched Polyionic Side Chains Macromolecules 44 2011 4742 4751 10.1021/ma200574d
26. J.M. Tour Conjugated Macromolecules of Precise Length and Constitution. Organic Synthesis for the Construction of Nanoarchitectures Chemical Reviews 96 1996 537 554 10.1021/cr9500287
27. P. Wautelet, M. Moroni, L. Oswald, J. Le Moigne, A. Pham, J.Y. Bigot, and S. Luzzati Rigid Rod Conjugated Polymers for Nonlinear Optics. 2. Synthesis and Characterization of Phenylene-Ethynylene Oligomers Macromolecules 29 1996 446 455 10.1021/ma950968t
28. L. Jones, J.S. Schumm, and J.M. Tour Rapid Solution and Solid Phase Syntheses of Oligo(1,4-phenylene ethynylene) s with Thioester Termini: Molecular Scale Wires with Alligator Clips. Derivation of Iterative Reaction Efficiencies on a Polymer Support Journal of Organic Chemistry 62 1997 1388 1410 10.1021/jo962336q
29. D.L. Pearson, and J.M. Tour Rapid Syntheses of Oligo(2,5-thiophene ethynylene) s with Thioester Termini: Potential Molecular Scale Wires with Alligator Clips Journal of Organic Chemistry 62 1997 1376 1387 10.1021/jo962335y
30. G. Klaener, and R.D. Miller Polyfluorene Derivatives: Effective Conjugation Lengths from Well-Defined Oligomers Macromolecules 31 1998 2007 2009 10.1021/ma971073e
31. C. Ferrante, U. Kensy, and B. Dick Does diphenylacetylene (tolan) fluoresce from its second excited singlet state? Semiempirical MO calculations and fluorescence quantum yield measurements Journal of Physical Chemistry 97 1993 13457 13463 10.1021/j100153a008
32. http://omlc.org/spectra/PhotochemCAD/html/114.html
33. A.G. Crawford, A.D. Dwyer, Z. Liu, A. Steffen, A. Beeby, L.-O. Palsson, D.J. Tozer, and T.B. Marder Experimental and Theoretical Studies of the Photophysical Properties of 2- and 2,7-Functionalized Pyrene Derivatives J. Am Chem. Soc. 133 2011 13349 13362 10.1021/ja2006862
34. W.F. Forbes, and M.B. Sheratte Light Absorption Studies: Part II. Ultraviolet Absorption Spectra of Substituted Benzoic Acids and Phenyl Benzoates Canadian Journal of Chemistry 33 1955 1829 1839 10.1139/v55-228
35. Principles of Fluorescence Spectroscopy J.R. Lakowicz 3rd ed. 2006 Springer New York
36. M. Levitus, K. Schmieder, H. Ricks, K.D. Shimizu, U.H.F. Bunz, and M.A. Garcia-Gariby Steps To Demarcate the Effects of Chromophore Aggregation and Planarization in Poly(phenyleneethynylene)s. 1. Rotationally Interrupted Conjugation in the Excited States of 1,4-Bis(phenylethynyl) benzene Journal of the American Chemical Society 123 2001 4259 4265 10.1021/ja003959v
37. C. Weder, and M.S. Wrighton Efficient Solid-State Photoluminescence in New Poly(2,5-dialkoxy-p-phenyleneethynylene)s Macromolecules 29 1996 5157 5165 10.1021/ma950902y
38. L. Prodi Luminescent chemosensors: from molecules to nanoparticles New Journal of Chemistry 29 2005 20 31 10.1039/B411758A
39. Topics in Fluorescence Spectroscopy C.D. Geddes, and J.R. Lakowicz "Advanced Concepts in Fluorescent sensing, Part A: Small Molecule Sensing" 9 2005 Springer New York