Metal complex of biscalix[4]arene derivative, and synthesis method and application thereof
A technology of aromatic hydrocarbon derivatives and metal complexes, applied in the field of medical biological detection, can solve the problems of unsuitability for labeling biomolecules and low sensitivity, and achieve the effects of simple and easy synthesis process, improved yield and high yield
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Embodiment 1
[0067] This embodiment provides a metal complex of a biscalix[4]arene derivative and a preparation method thereof. The biscalix[4]arene derivative has a molecular structure as shown in Formula I-1; the biscalix[4]arene derivative and rare earth metal ions Tb 3+ Coordinate to obtain complex, its molecular structure is as shown in formula II-1:
[0068]
[0069] Intermediate I'-1 was synthesized from intermediate E-1 and intermediate F-1, and intermediate I'-1 was oxidized to obtain biscalix[4]arene derivative I-1, biscalix[4]arene derivative I -1 complex rare earth metal ion Tb 3+ , to obtain biscalix [4] arene derivatives I-1 and Tb 3+ The complex II-1, the synthetic route is:
[0070]
[0071] (1) Preparation of Intermediate E-1
[0072] Step 1: Taking calix[4]arene as reaction raw material, get calix[4]arene (30.0g / 70.7mmol), anhydrous potassium carbonate (10.7g / 77.4mmol) and methyl p-toluenesulfonate (26.3g / 141.4mmol), dissolved in 500mL of CH 3 CN was refluxed...
Embodiment 2
[0100] This example provides a method for synthesizing the metal complex II-1 of biscalix[4]arene derivatives:
[0101] With Intermediate E-1, Intermediate E'-1 (equal to Intermediate E-1) and TsO-CH 2 -CH 2 -OsT synthesizes intermediate I'-1, intermediate I'-1 is oxidized to obtain biscalix[4]arene derivative I-1, biscalix[4]arene derivative I-1 is complexed with rare earth metal ion Tb 3+ , to obtain biscalix [4] arene derivatives I-1 and Tb 3+ The complex II-1, the synthetic route is:
[0102]
[0103] (1) Preparation of Intermediate E-1
[0104] Synthetic process is with the synthesis of the intermediate E-1 of embodiment 1, and intermediate E'-1 and intermediate E-1 are identical compound.
[0105] (2) Preparation of intermediate I'-1
[0106] Intermediate E-1 (0.8mmol), Intermediate E'-1 (1mmol) and K 2 CO 3 (7mmol) was dissolved in toluene, then added TsO-CH 2 -CH 2 -OsT (1.1mmol), under the protection of nitrogen, reflux at a temperature of 110°C for 2h, th...
Embodiment 3
[0112] This embodiment provides a metal complex of a biscalix[4]arene derivative and a preparation method thereof. The biscalix[4]arene derivative has a molecular structure as shown in Formula I-2; the biscalix[4]arene derivative and rare earth metal ions Eu 3+ Cooperate to obtain complex, its molecular structure is as shown in formula II-2:
[0113]
[0114] Synthesize intermediate I'-2 with intermediate E-2 and intermediate F-2 (the intermediate shown in formula F-2 is equivalent to the intermediate shown in formula F-1), after intermediate I'-2 is oxidized Two calix[4] arene derivatives I-2 are obtained, and two calix[4] arene derivatives I-2 are complexed with rare earth metal ions Eu 3+ , to obtain biscalix[4]arene derivative I-2 and Eu 3+ The complex II-2, the synthetic route is:
[0115]
[0116] (1) Preparation of Intermediate E-2
[0117] Step 1: Taking calix[4]arene as the reaction raw material, take calix[4]arene (30.0g / 70.7mmol), anhydrous potassium carbo...
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