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A molecular sensor with "off-on-off" fluorescence detection signal for acidic environment and its application
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A molecular sensor and signal detection technology, applied in fluorescence/phosphorescence, material analysis through optical means, instruments, etc., to achieve high yield, simple preparation process, and high application value
Active Publication Date: 2022-04-12
DEZHOU UNIV
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Problems solved by technology
However, molecular sensors constructed with fluorene fluorophores and sensitive to acidic environments with "off-on-off" dual fluorescence detection signals have not been reported yet.
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Embodiment 1
[0025] in N 2 Under protective conditions, put 2 mmol of p-dianilinobenzaldehyde in a 50 mL round bottom flask filled with 10 mL of absolute ethanol and raise the temperature to 75°C; dissolve 1 mmol of 2,7-diaminofluorene in 10 mL of anhydrousEthanol, and slowly drop it into the above-mentioned p-dianilinobenzaldehyde solution, continue to heat the reaction for 6 hours; filter the reaction mixture, wash with absolute ethanol, and dry to obtain yellow-brown powderCompound A, 338.9 mg , and the yield was 48%.
Embodiment 2
[0027] in N 2 Under protective conditions, put 2 mmol of p-dianilinobenzaldehyde into a 50 mL round-bottomed flask filled with 10 mL of absolute ethanol and raise the temperature to 75°C; dissolve 1 mmol of 2,7-diaminofluorene in 10 mL of anhydrousEthanol, and slowly drop it into the above-mentioned p-dianilinobenzaldehyde solution, and continue to heat the reaction for 8 hours; after the reaction mixture was filtered, washed with absolute ethanol, and dried, tan powdery compound B was obtained, 339 mg , and the yield was 48%.
Embodiment 3
[0029] in N 2 Under protective conditions, put 2 mmol of p-dianilinobenzaldehyde in a 50 mL round bottom flask filled with 10 mL of absolute ethanol and raise the temperature to 75°C; dissolve 1 mmol of 2,7-diaminofluorene in 10 mL of anhydrous After adding ethanol and slowly adding it to the p-dianilinobenzaldehyde solution, then adding 2 mmol glacial acetic acid, and continuing the reaction for 6 hours; the reaction mixture was filtered, washed with absolute ethanol, and dried to obtain a yellow-brown powder compound C, 340 mg, yield 48.2%.
[0030] The compound A, B and C that embodiment 1-3 obtains respectively is analyzed and measured, and the proton nuclear magnetic spectrum of the three Figure 1 To, the data are as follows: in 1 H NMR (CDCl 3 , 400 MHz), including 2 C=N-carbon protonsignal peaks: 8.58 (s, 2H); 34 aromatic ring proton signal peaks: 7.88 (d, 2H ), 7.82 (d, 4H ), 7.47 ( s, 2H), 7.41 (t, 8H ), 7.28 (d, 2H ), 7.18 (m, 12H), 6.98 (d, 4H ); 2 CH 2 -Prot...
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Abstract
The invention relates to the technical field of organic compound performance, and discloses a triphenylamine-fluorenemolecular sensor, which uses 2,7-diaminofluorene and p-dianilinobenzaldehyde as reaction raw materials, and is based on a one-step polymerization reaction between aldehydes and ammonia preparation. Since the molecular sensor contains two types of proton interaction sites, diphenylamine and imine, it exhibits sensitive "off-on-off" dual fluorescence detection signals for acidic environments, with high sensitivity and good selectivity, and has significant applications value; and its preparation method has the advantages of high yield, simple preparation process, easy implementation, etc., is suitable for industrial promotion, and creates favorable conditions for the popularization and application of this triphenylamine-fluorenemolecular sensor.
Description
technical field [0001] The invention relates to the functional technical field of organic compounds, in particular to a triphenylamine-fluorene molecular sensor with sensitive "off-on-off" fluorescence detection signals for acidic environments and its application. Background technique [0002] With the development of society, the accurate measurement of pH value, which is closely related to the fields of human work and life, life science and medicine, has become one of the main issues that people focus on. In the process of industrial and agricultural production, specific acid and alkaline environments are often required. However, when wastewater with high acidity or high alkalinity is discharged into nature, it will cause serious pollution to the entire water system and soil, and bring great harm to the ecosystem and human living environment. In addition, the human body usually maintains a constant pH environment in the organism through the buffer system of the body fluid ...
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