Fluorescent compound, fluorescent probe and fluorescent sensing film as well as preparation method and application of fluorescent compound, fluorescent probe and fluorescent sensing film
A fluorescent compound and fluorescent sensing technology, applied in the field of fluorescent compounds, can solve problems such as unsatisfactory real-time online detection, bulky equipment, cumbersome operation, etc.
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[0042] The synthesis route of the fluorescent compound with sensing function for water vapor and micro-trace water in organic solvents disclosed by the present invention is as follows: Figure 7 As shown, the preparation method of the fluorescent compound specifically includes the following steps:
[0043] S1: Add N-(tert-butoxycarbonyl)alkyldiamine and 4-bromo-1,8-naphthalene dicarboxylic anhydride to absolute ethanol, heat to 80-85°C and reflux for 12-15 hours, then naturally cool to room temperature , solid-liquid separation, repeated washing of the solid with absolute ethanol, and drying to obtain solid compound a, wherein the structural formula of N-(tert-butoxycarbonyl)alkyldiamine is In the formula, n=1, 2, 3, 4, 5, 6, 7 or 8; the reaction equation of this step is as follows:
[0044]
[0045] In order to increase the reaction rate and conversion rate of raw materials, suppress side reactions and avoid excessive waste of raw materials, N-(tert-butoxycarbonyl) alkyl...
Embodiment 1
[0071] This embodiment provides a fluorescent compound, the structural formula of which is:
[0072]
[0073] The preparation method of this compound specifically comprises the following steps:
[0074] S1: Add 1.6g N-(tert-butoxycarbonyl)-1,2-diaminoethane and 2.77g 4-bromo-1,8-naphthalene dicarboxylic anhydride to 50mL absolute ethanol, heat to 80°C and reflux After 12 hours, naturally cool to room temperature, filter and repeatedly wash the resulting solid with numerous ethanol, and dry in vacuo to obtain light yellow needle-like solid compound a with a yield of 90%, wherein N-(tert-butoxycarbonyl)-1,2-diamino The mass ratio of ethane, 4-bromo-1,8-naphthalene dicarboxylic anhydride and absolute ethanol is 1:1:85.
[0075] S2: 2.1 g of the needle-like solid compound a obtained in S1 was added to 60 ml of ethylene glycol monomethyl ether solution, and 5.41 g of 2-aminomethylpyridine was added at room temperature. After reflux for 24h, cool down to room temperature natura...
Embodiment 2
[0079] This embodiment provides a fluorescent compound, the structural formula of which is:
[0080]
[0081] The preparation method of this compound is compared with Example 1, S1~S3 is consistent with Example 1, and the specific operation method of S4 is:
[0082]1.73 g of compound c obtained from S3 was dissolved in 300 ml of tetrahydrofuran, and 0.62 g of hexyl isocyanate was added to the solution, and stirred at room temperature for 6 h. Suction filtration after the reaction, repeated washing of the obtained solid with n-hexane, vacuum drying to obtain the fluorescent compound with a yield of 88%, wherein the ratio of compound c, hexyl isocyanate and tetrahydrofuran is 1:1 : 700. Among them, the mass spectrometry detection result of the fluorescent compound is: ESI-HRMS (m / z): [M+Na] + calcd:496.2325,found:496.23248; 1 H NMR (400MHz, DMSO) δ8.77(d, J=8.4Hz, 1H), 8.58(d, J=4.3Hz, 1H), 8.51(d, J=5.7Hz, 1H), 8.46(d, J =7.2Hz, 1H), 8.18(d, J=8.5Hz, 1H), 7.76(t, J=7.8Hz...
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