Synthesis and property of solvatochromic fluorophore based on D-pi-A molecular system: 2-[[3-cyano-4-(N-ethyl-N-(2-hydroxyethyl)amino)styryl]-5,5-dimethylfuran-2(5H)-ylidene]malononitrile dye.
2-[[3-Cyano-4-(N-ethyl-N-(2-hydroxyethyl)amino)styryl]-5,5-dimethylfuran-2(5H)-ylidene]malononitrile styryl dye was prepared by the condensation of 4-[(2-hydroxy-ethyl)-methyl-amino]-benzaldehyde (donor moiety) with 2-cyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (acceptor moiety). The corresponding design, synthesis and solvatochromic characteristics of the intramolecular charge-transfer (ICT) dye chromophore were discussed and determined. Optical properties such as absorption and fluorescence emission spectra were monitored in several solvent media with different polarity. In this determination, the prepared dye chromophore showed positive solvatochromism effect and the resulting solvatochromic characteristics were studied with semiempirical calculations. The energy potentials of this dye chromophore such as HOMO and LUMO values were calculated by computational simulation approaches using Material Studio 4.3. Furthermore, the functions as a molecular switching sensor with pH stimulation of alkali-acid addition were determined in DMSO, which was operated by deprotonation/protonation effects based on intramolecular charge-transfer system.
Son
Young-A
YA
Department of Advanced Organic Materials and Textile Systmem Engineering, Chungnam National University, Daejeon, South Korea.
Gwon
Seon-Yeong
SY
Lee
Sue-Yoen
SY
Kim
Sung-Hoon
SH
D000042:Absorption; D003198:Computer Simulation; D005456:Fluorescent Dyes / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010777:Photochemistry; D012997:Solvents / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
D005456:Fluorescent Dyes; D009570:Nitriles; D012997:Solvents; C000945:dicyanmethane