Room-temperature phosphorescence in solution and in solid state from purely organic dyes

Dyes and Pigments

Volumn 95, Issue 2, 2012, Pages 161-167

  Yong, Guoping ^a   She, Wenlong ^a   Zhang, Yiman ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

(E) 3 benzylideneimidazo 1,2 a pyridin 2(3H) one derivatives; One pot synthesis; Phosphorescent colors; Phosphorescent dyes; Room temperature phosphorescence; Solid state

Indexed keywords

COLOR CHANGES; COLUMNAR STACKING; INTERMOLECULAR HYDROGEN BONDING; ONE-POT SYNTHESIS; ORGANIC DYE; PHOSPHORESCENT DYES; POTENTIAL APPLICATIONS; ROOM TEMPERATURE; ROOM TEMPERATURE PHOSPHORESCENCE;

HYDROGEN BONDS; LIGHT EMITTING DIODES; MOLECULES; PHOSPHORESCENCE; PHOSPHORS;

LIGHT EMISSION;

EID: 84861211124     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2012.04.003     Document Type: Article

References (37)

1. J.B. Birks Photophysics of aromatic molecules 1970 Wiley London, UK
2. J. Malkin Photophysical and photochemical properties of aromatic compounds 1992 CRC Boca Raton, FL
3. R. Jakubiak, Z. Bao, and R. Rothberg Dendritic side groups as three-dimensional barriers to aggregation quenching of conjugated polymer fluorescence Synth Met 114 2000 61 64
4. L. Chen, S. Xu, D. McBranch, and D. Whitten Tuning the properties of conjugated polyelectrolytes through surfactant complexation J Am Chem Soc 122 2000 9302 9303
5. S. Hecht, and J.M.J. Frechet Dendritic encapsulation of function: applying nature's site isolation principle from biomimetics to materials science Angew Chem Int Ed 40 2001 74 91
6. S. Setayesh, A.C. Grimsdale, T. Weil, V. Enkelmann, K. Müllen, and F. Meghdadi Polyfluorenes with polyphenylene dendron side chains: toward non-aggregating, light-emitting polymers J Am Chem Soc 123 2001 946 953
7. B.S. Gaylord, S. Wang, A.J. Heeger, and G.C. Bazan Water-soluble conjugated oligomers: effect of chain length and aggregation on photoluminescence-quenching efficiencies J Am Chem Soc 123 2001 6417 6418
8. J.D. Luo, Z.L. Xie, J.W.Y. Lam, L. Cheng, H.Y. Chen, and C.F. Qiu Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole Chem Commun 2001 1740 1741
9. B.K. An, S.K. Kwon, S.D. Jung, and S.Y. Park Enhanced emission and its switching in fluorescent organic nanoparticles J Am Chem Soc 124 2002 14410 14415
10. J. Chen, C.C.W. Law, L.W.Y. Lam, Y.Q. Dong, S.M.F. Lo, and I.D. Williams Synthesis, light emission, nanoaggregation, and restricted intramolecular rotation of 1,1-substituted 2,3,4,5-tetraphenylsiloles Chem Mater 15 2003 1535 1546
11. Z. Li, Y.Q. Dong, J.W.Y. Lam, J.X. Sun, A.J. Qin, and M. Haëussler Functionalized siloles: versatile synthesis, aggregation-induced emission, and sensory and device applications Adv Funct Mater 19 2009 905 917
12. Y.N. Hong, J.W.Y. Lam, and B.Z. Tang Aggregation-induced emission: phenomenon, mechanism and applications Chem Commun 2009 4332 4353
13. M.A. Baldo, M.E. Thompson, and S.R. Forrest Phosphorescent materials for application to organic light emitting devices Pure Appl Chem 71 1999 2095 2106
14. A. Kohler, J.S. Wilson, and R.H. Friend Fluorescence and phosphorescence in organic materials Adv Mater 14 2002 701 707
15. A.P. De Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, and J.T. Rademacher Signaling recognition events with fluorescent sensors and switches Chem Rev 97 1997 1515 1566
16. M.A. Baldo, D.F. O'Brien, Y. You, A. Shoustikov, S. Sibley, and M.E. Thompson Highly efficient phosphorescent emission from organic electroluminescent devices Nature 395 1998 151 154
17. W.L. Rumsey, J.M. Vanderkooi, and D.F. Wilson Imaging of phosphorescence: a novel method for measuring oxygen distribution in perfused tissue Science 241 1988 1649 1651
18. Y. Shao, and Y. Yang Efficient organic heterojunction photovoltaic cells based on triplet materials Adv Mater 17 2005 2841 2844
19. G. Zhang, G.M. Palmer, M.W. Dewhirts, and C.L. Fraser A dual-emissive-materials design concept enables tumour hypoxia imaging Nat Mater 8 2009 747 751
20. WZ. Yuan, X.Y. Shen, H. Zhao, J.W.Y. Lam, L. Tang, and P. Lu Crystallization-induced phosphorescence of pure organic luminogens at room temperature J Phys Chem C 114 2010 6090 6099
21. O. Bolton, K. Lee, H.J. Kim, K.Y. Lin, and J. Kim Activating efficient phosphorescence from purely organic materials by crystal design Nat Chem 3 2011 205 210
22. G.P. Yong, C.F. Li, Y.Z. Li, and S.W. Luo New zwitterionic radical salts: dimers in solution and unusual magnetic and luminescent properties in the solid state Chem Commun 46 2010 3194 3196
23. Y.Z. Li, G.P. Yong, Y.M. Zhang, C.F. Li, and W.L. She 3-Carbaldehyde-substituted 2,3′-biimidazo[1,2-a]pyridin-2′-one radicals: Interesting π-stacking structures and magnetic properties Synth Met 161 2011 713 717
24. Y.M. Zhang, G.P. Yong, C.F. Li, W.L. She, and Y.Z. Li The zwitterionic radical and its neutral radical derivative with interesting magnetic properties Synth Met 161 2012 2708 2713
25. G.P. Yong, S. Qiao, and Z.Y. Wang A one-dimensional coordination polymer based on novel radical anion ligand generated in situ: notable magnetic and luminescence properties Cryst Growth Des 8 2008 1465 1467
26. II compounds exhibiting terminal anion ligand induced direct white-light-emission Dalton Trans 40 2011 4131 4139
27. G.P. Yong, Y.Z. Li, W.L. She, and Y.M. Zhang Isostructural metal-anion radical coordination polymers with tunable phosphorescent colors (deep blue, blue, yellow, and white) induced by terminal anions and metal cations Chem Eur J 17 2011 12495 12501
28. G.P. Yong, Y.Z. Li, Y.M. Zhang, and W.L. She Magnetic and luminescent properties of Cd(II)- and Fe(II)-anion radical frameworks: various networks or structures influenced by metal ion sizes or in situ forming mechanisms of anion radical ligand Cryst Eng Comm 14 2012 1439 1448
29. G.P. Yong, Y.M. Zhang, W.L. She, and Y.Z. Li Stacking-induced white-light and blue-light phosphorescence from purely organic radical materials J Mater Chem 21 2011 18520 18522
30. D.R. Kearns, and W.A. Case Investigation of singlet→triplet transitions by the phosphorescence excitation method. III. Aromatic ketones and aldehydes J Am Chem Soc 88 1966 5087 5097
31. T. Itoh The evidence showing that the intersystem crossing yield of benzaldehyde vapour is unity Chem Phys Lett 151 1988 166 168
32. F. Reindel, and A. Von Putzer-Reybegg Über die umsetzungs-produkte von pyrimidazolon-2 mit aromatischen aldehyden und ringförmigen 1,2-dicarbonylverbindungen Ber Dtsch Chem Ges 59 1926 2926 2932
33. R.A. Abramovitch, and D.H. Hey The condensation of 2,3-dihydro-2- oxoimidazo [1,2-a]pyridine with o-nitrobenzaldehyde J Chem Soc C 1966 1095 1096
34. C.F. Li, G.P. Yong, and Y.Z. Li Phosphorescent iridium (III) 2-phenylpyridine complexes: efficient color tuning by novel ancillary ligands Inorg Chem Commun 13 2010 179 182
35. G.M. Sheldrick SHELXL-97 and SHELXS-97 1998 University of Göttingen Göttingen, Germany
36. K.C. Stylianou, R. Heck, S.Y. Chong, J. Bacsa, J.T.A. Jones, and Y.Z. Khimyak A guest-responsive fluorescent 3D microporous metal-organic framework derived from a long-lifetime pyrene core J Am Chem Soc 132 2010 4119 4130
37. S.H. Kim, S. Park, J.E. Kwon, and S.Y. Park Organic light-emitting diodes with a white-emitting molecule: emission mechanism and device characteristics Adv Funct Mater 21 2011 644 651