Metal complexes of bicalix[4]arene derivatives and their synthesis methods and applications
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
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Embodiment 1
[0068] 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:
[0069]
[0070] 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:
[0071]
[0072] (1) Preparation of Intermediate E-1
[0073] 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
[0099] This example provides a method for synthesizing the metal complex II-1 of biscalix[4]arene derivatives:
[0100] 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:
[0101]
[0102] (1) Preparation of Intermediate E-1
[0103] 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.
[0104] (2) Preparation of intermediate I'-1
[0105] 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 105°C for 3h, then add a certain ...
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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