π-Expanded Ketocoumarins as Efficient, Biocompatible Initiators for Two-Photon-Induced Polymerization

作者: Rashid Nazir , Paulius Danilevicius , Adina I. Ciuciu , Maria Chatzinikolaidou , David Gray

DOI: 10.1021/CM500612W

关键词: PolymerizationAlkylAbsorption (chemistry)FluorescenceConjugated systemAmine gas treatingPhotochemistrySolubilityChromophoreChemistry

摘要: A series of π-expanded coumarins comprising 4–5 conjugated rings were designed and synthesized. The strategic placement two dialkylamino groups containing long alkyl chains attached to the peripheral ends bis-coumarins resulted in dyes with superb solubility. As α,β-unsaturated ketones, these compounds display properties donor–acceptor–donor (D–A–D)-type chromophores. Photophysical studies new functional revealed a combination favorable properties: strong absorption blue green light, weak fluorescence, reasonable two-photon (2PA) cross-section, complete solubility nonpolar solvents. fluorescence lifetimes coumarin-derived ketones measured for first time. amine at positions produced cross-section values level 150–400 GM around 800 nm, which generated photoinitiation. highest 2PA was approximately 400 de...

参考文章(49)
Dnolad P. Specht, Peter A. Martic, Samir Farid, Ketocoumarins Tetrahedron. ,vol. 38, pp. 1203- 1211 ,(1982) , 10.1016/0040-4020(82)85104-1
Ken-ichi Watanabe, Atsushi Imazawa, Aldol Condensations Catalyzed by Co(II) Complexes of Pyridine-containing Copolymers Bulletin of the Chemical Society of Japan. ,vol. 55, pp. 3208- 3211 ,(1982) , 10.1246/BCSJ.55.3208
Fuying Hao, Zhaodi Liu, Mingliang Zhang, Jie Liu, Shengyi Zhang, Jieying Wu, Hongping Zhou, YuPeng Tian, Four new two-photon polymerization initiators with varying donor and conjugated bridge: Synthesis and two-photon activity Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. ,vol. 118, pp. 538- 542 ,(2014) , 10.1016/J.SAA.2013.09.051
James Wojtyk, Andrew McKerrow, Peter Kazmaier, Erwin Buncel, Quantitative investigations of the aggregation behaviour of hydrophobic anilino squaraine dyes through UV/vis spectroscopy and dynamic light scattering Canadian Journal of Chemistry. ,vol. 77, pp. 903- 912 ,(1999) , 10.1139/V99-073
Ryan Davis, Umashankar Das, Hilary Mackay, Toni Brown, Susan L. Mooberry, Jonathan R. Dimmock, Moses Lee, Hari Pati, Syntheses and cytotoxic properties of the curcumin analogs 2,6-bis(benzylidene)-4-phenylcyclohexanones. Archiv Der Pharmazie. ,vol. 341, pp. 440- 445 ,(2008) , 10.1002/ARDP.200800028
Aleksandr Ovsianikov, Jacques Viertl, Boris Chichkov, Mohamed Oubaha, Brian MacCraith, Ioanna Sakellari, Anastasia Giakoumaki, David Gray, Maria Vamvakaki, Maria Farsari, Costas Fotakis, Ultra-low shrinkage hybrid photosensitive material for two-photon polymerization microfabrication. ACS Nano. ,vol. 2, pp. 2257- 2262 ,(2008) , 10.1021/NN800451W
Shoji Maruo, Osamu Nakamura, Satoshi Kawata, Three-dimensional microfabrication with two-photon-absorbed photopolymerization. Optics Letters. ,vol. 22, pp. 132- 134 ,(1997) , 10.1364/OL.22.000132
Yun-Sheng Chen, Amir Tal, Stephen M. Kuebler, Route to Three-Dimensional Metallized Microstructures Using Cross-Linkable Epoxide SU-8 Chemistry of Materials. ,vol. 19, pp. 3858- 3860 ,(2007) , 10.1021/CM0710812
J. K. Gansel, M. Thiel, M. S. Rill, M. Decker, K. Bade, V. Saile, G. von Freymann, S. Linden, M. Wegener, Gold Helix Photonic Metamaterial as Broadband Circular Polarizer Science. ,vol. 325, pp. 1513- 1515 ,(2009) , 10.1126/SCIENCE.1177031
Niklas Pucher, Arnulf Rosspeintner, Valentin Satzinger, Volker Schmidt, Georg Gescheidt, Jürgen Stampfl, Robert Liska, Structure−Activity Relationship in D-π-A-π-D-Based Photoinitiators for the Two-Photon-Induced Photopolymerization Process Macromolecules. ,vol. 42, pp. 6519- 6528 ,(2009) , 10.1021/MA9007785