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Asymmetric photoelectric active thiacalixarene [4] acceptor molecule and compounding method thereof

A synthesis method, a technology of aromatic hydrocarbon receptors, applied in chemical instruments and methods, luminescent materials, fluorescence/phosphorescence, etc., can solve the problems of limited application scope and difficult to achieve effective detection, etc.

Active Publication Date: 2017-12-15
SHANDONG NORMAL UNIV
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the use of this design strategy results in the vast majority of thiacalix[4]arene-based receptor molecules having a symmetrical structure and containing only a single optical or electrical signal responsive group, making it difficult to achieve a dual-channel response using light and electricity. Efficient detection of specific substrates, limiting its range of applications

Method used

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  • Asymmetric photoelectric active thiacalixarene [4] acceptor molecule and compounding method thereof
  • Asymmetric photoelectric active thiacalixarene [4] acceptor molecule and compounding method thereof
  • Asymmetric photoelectric active thiacalixarene [4] acceptor molecule and compounding method thereof

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preparation example Construction

[0026] In a preferred embodiment of the present invention, a method for synthesizing the above-mentioned asymmetric optical and electroactive thiacalix[4]arene receptor molecule Fc-TA-RB is also provided, which method comprises:

[0027] Selective acylation of tert-butylthiacalix[4]arene-1,3-diamine with ferrocene carboxylic acid chloride to synthesize monoferrocene formamide intermediate TA-Fc, and then acylate with rhodamine B acid chloride The reaction produces the receptor molecule Fc-TA-RB.

[0028] The synthesis reaction formula is as follows:

[0029]

[0030] In the formula: (a) includes ferrocene carbonyl chloride, alkali, organic solvent and reaction temperature; (b) includes rhodamine B acid chloride, alkali, organic solvent and reaction temperature.

[0031] In the above synthesis method, p-tert-butylthiacalix[4]arene-1,3-diamine, ferrocene formyl chloride, and rhodamine B acid chloride are existing substances that can be prepared by conventional methods by those skilled i...

Embodiment 1

[0054] Synthesis of intermediate TA-Fc

[0055] Under a nitrogen atmosphere, a solution of ferrocene carbonyl chloride (0.075g, 0.30mmol) in dichloromethane (10.0mL) was slowly added dropwise to the p-tert-butylthiacalix[4]arene-1,3-bisamine ( 0.202g, 0.250mmol) and triethylamine (0.5mL) in dichloromethane (10.0mL) solution, about 4h to finish dropping. After the reaction, the reaction solution was poured into ice water, extracted with dichloromethane, washed with saturated sodium bicarbonate and brine successively, the organic phase was dried over anhydrous magnesium sulfate, filtered and the solvent was evaporated under reduced pressure, and the residue was separated by column chromatography (Dichloromethane / methanol, 30:1, v / v, R f = 0.3), 0.207 g of TA-Fc yellow solid was obtained, and the yield was 73%. 1 HNMR(300MHz, CDCl 3 ,TMS): δ0.82 (s, 9H, t-Bu), 1.06 (s, 9H, t-Bu), 1.34 (s, 18H, t-Bu), 3.29-3.32 (m, 2H, CH 2 ),4.02-4.03(m,2H,CH 2 ),4.21(s,5H,Cp-H), 4.27(s,2H,Cp-H), 4....

Embodiment 2

[0057] Synthesis of target receptor molecule Fc-TA-RB

[0058] Under a nitrogen atmosphere, to the intermediate TA-Fc (0.360g, 0.36mmol) and triethylamine (1mL) in dichloromethane (15.0mL) solution was slowly added dropwise rhodamine B acid chloride (0.250g, 0.54mmol) Dichloromethane (15.0 mL) solution was dropped in about 4 hours, and the reaction was stirred at room temperature for 12 hours. After the reaction, the reaction solution was poured into ice water, extracted with dichloromethane, washed with saturated sodium bicarbonate and brine successively, the organic phase was dried over anhydrous magnesium sulfate, filtered and the solvent was evaporated under reduced pressure, and the residue was separated by column chromatography (Ethyl acetate / petroleum ether, 1:2, v / v, R f =0.5), 0.262 g of Fc-TA-RB yellow solid was obtained, and the yield was 51%. 1 H NMR(300MHz, CDCl 3 ,TMS): δ0.77(s,9H,t-Bu),0.82(s,9H,t-Bu),1.14(t,12H,J=6.8Hz,CH 3 ), 1.34 (s, 18H, t-Bu), 3.29 (q, 8H, J =...

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Abstract

The invention discloses an asymmetric photoelectric active thiacalixarene [4] acceptor molecule and a compounding method thereof. The method is characterized by successfully compounding the asymmetric photoelectric active thiacalixarene [4] acceptor molecule containing ferrocene and rhodamine b groups by successively introducing an electrochemical probe and a fluorescence probe into a thiacalixarene [4] structure platform by utilizing asymmetric design and then performing stepping selective acylation reaction of thiacalixarene [4]-1,3-diamine. The technique according to the invention supplies a new method for designing and compounding the asymmetric photoelectric active thiacalixarene [4] acceptor molecule with photoresponse center and electroresponse center, establishes a basis for realizing the photoelectric two-channel response detection for the acceptor molecule and has significance in expanding the application thereof in super-molecular recognition.

Description

Technical field [0001] The invention belongs to the field of organic synthetic chemistry, and specifically relates to an asymmetric photoelectrically active thiacalix[4] arene receptor molecule and a synthesis method thereof. Background technique [0002] Molecular recognition is one of the core contents of supramolecular chemistry research, and it is an important basis for information storage, replication and transmission of natural organisms. In particular, molecular recognition research based on light and electrical active receptors has become a hot area of ​​supramolecular chemistry. . Thiacalix[4]arene has the characteristics of variable conformation, adjustable cavities, and multiple structural modification sites. It is a promising platform for the design and construction of receptor molecules and has a wide range of uses, especially based on thiacalix[ 4] The design, synthesis and functional research of the photo- and electroactive receptor molecules of aromatic hydrocarb...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02C09K11/06G01N27/26G01N21/64
CPCC07F17/02C09K11/06C09K2211/187G01N21/64G01N27/26
Inventor 郭佃顺吕雪欣郭玉双赵乐姜国静
Owner SHANDONG NORMAL UNIV
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