Proton-induced fluorescent switching of a new 2D-pi-A type vinylcyanoacetate-pyran dye.
A new 2D-pi-A type vinylcyanoacetate-pyran dye, ethyl 2-(2,6-bis(2-butoxy-4-(diethylamino)styryl)-4H-pyran-4-ylidene)-2-cyanoacetate (BDPC) was prepared by condensation reaction. The chemical structures of all the intermediates and the BDPC dye are characterized by (1)H NMR, MS. It showed interestingly solvatochromic and solvatofluorchromic properties in various solvents. Its LUMO and HOMO values were obtained by the theoretical calculation. The fluorescent intensity of BDPC dye can be reversibly selected by protonation/deprotonation of the amine moiety via control of intramolecular charge transfer (ICT), leading to a fluorescent molecular switch with two distinguished "on" and "off" states.
Wang
Sheng
S
Department of Textile System Engineering, Kyungpook National University, Daegu 702-701, Republic of Korea.
Kim
Sung-Hoon
SH
D000042:Absorption; D004396:Coloring Agents / Q000138:chemical synthesis / Q000737:chemistry*; D004579:Electron Transport; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D008970:Molecular Weight; D011522:Protons; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet
D004396:Coloring Agents; D011522:Protons; D011714:Pyrans; D012997:Solvents