期刊
TETRAHEDRON
卷 67, 期 23, 页码 4236-4242出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.04.023
关键词
Photochromism; Diarylethene; Rhodamine; Molecular switch
资金
- National Natural Science Foundation of China [20962008]
- New Century Excellent Talents in University [NCET-08-0702]
- Project of Jiangxi Academic and Technological Leader [2009DD00100]
- Natural Science Foundation of Jiangxi Province [2009GZH0034, 2009GQH0036, 2010GQH0038]
- Jiangxi Education Office [GJJ11026]
A novel fluorescent switch based on rhodamine B and photochromic diarylethene, 1-[2-methyl-5-(4-methoxylphenyl)-3-thienyl]-2-[2-methyl-5-(4-rhodamine B hydrazine-Schiff base-phenyl)-3-thienyl]perfluorocyclopentene (1), has been successfully synthesized through the condensation of rhodamine B hydrazine and 1-[2-methyl-5-(4-methoxylphenyl)-3-thienyl]-2-[2-methyl-5-(4-formylphenyl)-3-thienyl] perfluorocyclopentene. UV and FL measurements reveal that the compound exhibits good photochromic properties responsive to proton and optic dual inputs. Upon irradiation with 297 nm light, the colorless solution of compound 1 turns blue, while the blue solution becomes colorless after irradiated with visible light (lambda>450 nm). Furthermore, upon an addition of H+, the fluorescence resonance energy transfers from the rhodamine unit (FRET donor) to the closed-ring diarylethene unit (FRET acceptor), although no energy transfer occurs when the diarylethene is in the open-ring form. The emission intensity of the rhodamine can be modulated with proton and UV/vis light and molecular-level signal communication has been constructed, indicating high potentials of the compound in molecular switches or naked eye recognition systems. (C) 2011 Elsevier Ltd. All rights reserved.
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