A proton and optic dual-control molecular switch based on photochromic diarylethene bearing a rhodamine unit

作者：Liu, Weijun; Pu, Shouzhi^*; Cui, Shiqiang; Liu, Gang; Fan, Congbin

来源：Tetrahedron, 2011, 67(23): 4236-4242.

DOI：10.1016/j.tet.2011.04.023

• Photochromism
• Diarylethene
• Rhodamine
• Molecular switch

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.

• 出版日期2011-6-10
• 单位江西科技师范大学