A kind of acylhydrazone molecular switch, its preparation method and application
A technology of compound and general formula, which is applied in the field of acylhydrazone molecular switch and its preparation, can solve the problems of low E-Z conversion rate, no reports of loading and controlled release, low photo-induced E-Z conversion rate, etc.
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Embodiment 1
[0058] Molecular switch I (in general formula (I), R 1 =R 2 =R 3 =-(OCH 2 CH 2 ) 5 OH; R 4 =CH 3 ; 5 = H; R 6 =-OCH 2 (CH 2 ) 12 CH 3 )Synthesis:
[0059]
[0060] A compound of formula (II) (0.2-2 g) and ethanol (10-50 mL) were added to a round bottom flask, followed by a solution of compound of formula (III) (0.3-5 g) in ethanol (10-50 mL). After heating and stirring at 40-80°C for 1-10min, filter. The collected solids were washed with ethanol to obtain the compound of formula (I) in greater than 95% yield.
[0061] Formula (I) compound in DMSO-d6 1 H-NMR spectrum see figure 2 , 13 C-NMR spectrum see image 3 , HRMS spectrum see Figure 4 .
Embodiment 2
[0063] The compound of formula I (in general formula (I), R 1 =R 2 =R 3 =-(OCH 2 CH 2 ) 5 OH; R 4 =CH 3 ; 5 = H; R 6 =-OCH 2 (CH 2 ) 12 CH 3 ) was dissolved in water, and the obtained aqueous solution was irradiated with 365nm light of a portable ultraviolet lamp to measure the 1 H-NMR spectrum, 90% of the E-isomer was converted to the Z-isomer. its in D 2 Before and after illumination in O 1 H-NMR spectrum, see Figure 5 .
Embodiment 3
[0065] Compounds of formula (I) (in general formula I, R 1 =R 2 =R 3 =-(OCH 2 CH 2 ) 5 OH; R 4 =CH 3 ; 5 = H; R 6 =-OCH 2 (CH 2 ) 12 CH 3 ) is dissolved in DMSO, with 388nm ultraviolet light for different time, measure the ultraviolet-visible spectrum of different light time, see Figure 6 (a); It is found that the absorption band at 377nm gradually weakens, while the absorption band at 273nm gradually increases, see Figure 6 (b).
[0066] Figure 6 is a compound of formula (I) (in general formula I, R 1 =R 2 =R 3 =-(OCH 2 CH 2 ) 5 OH; R 4 =CH 3 ; 5 = H; R 6 =-OCH 2 (CH 2 ) 12 CH 3 ) UV-Vis spectra in DMSO as a function of illumination time (a) and absorbance at 377nm and 273nm as a function of illumination time (b). [Formula I]=6.0×10 -5 M, light source 388nm light.
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