Thiol spirothiopyran compound and preparation method and application thereof
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A compound and mercapto spiro technology, which are applied in the fields of mercapto spiro thiopyran compounds and their preparation and application, and achieve the effects of good binding ability, low cost and simple synthesis method
Active Publication Date: 2014-07-30
INST OF CHEM CHINESE ACAD OF SCI
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At present, the application of this kind of materials is limited to the internal doping of semiconductor components and the semiconductor / dielectric layer interface (Zhang H.T., Guo X.F., Hui J.S., Hu S.X., Xu W., Zhu D.B., Nano Lett., 2011 , 11, 4939-4946), however, the research work on making OFET with photoresponsive function by assembling spirothiopyran molecules at the semiconductor / metal electrode interface has not been reported yet.
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Embodiment 1
[0038] Example 1, Synthesizing the compound shown in formula a and preparing p-type photoelectric function organic field effect transistor
[0039]
[0040] formula a
[0041] (1) compound shown in synthetic formula a:
[0042] Under the protective condition of nitrogen, bromododecyl N-substituted indole (R 1 =-C 12 h 24 ) (4.052g, 10mmol) and o-aldehyde p-nitrothiophenol (2.198g, 12mmol) were dissolved in ethanol (30mL), heated to 60°C, stirred for 5 hours; the system was cooled to room temperature, filtered, and the obtained Solid is the compound shown in formula III (R 1 =-C 12 h 24 ), dissolve the compound shown in formula III in ethanol, add potassium thioacetate (3.426g, 30mmol), heat up to 60°C, stir for 0.5 hour, cool to room temperature, filter, add potassium hydroxide in the filtrate, stir, Spin to dry the ethanol solvent, dissolve the solid in dichloromethane, add dilute hydrochloric acid with pH = 4.0 to the solution, separate and extract, combine the org...
Embodiment 2
[0054] Example 2, Synthesizing the compound shown in formula b and preparing p-type photoelectric function organic field effect transistor
[0055]
[0056] formula b
[0057] (1) compound shown in synthetic formula b:
[0058] Under the protective condition of nitrogen, bromododecyl N substituted indole (R 1 =-C 16 h 32 ) (4.613g, 10mmol) and o-aldehyde p-nitrothiophenol (2.198g, 12mmol) were dissolved in ethanol (30mL), heated to 60°C, and stirred for 5 hours; the system was cooled to room temperature, filtered, and the obtained Solid is the compound shown in formula III (R 1 =-C 16 h 32 ), dissolve the compound shown in formula III in ethanol, add potassium thioacetate (3.426g, 30mmol), heat up to 60°C, stir for 0.5 hour, cool to room temperature, filter, add potassium hydroxide in the filtrate, stir, Spin to dry the ethanol solvent, dissolve the solid in dichloromethane, add dilute hydrochloric acid with pH = 4.0 to the solution, separate and extract, combine the...
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Abstract
The invention discloses a thiol spirothiopyran compound shown in the formula I, and a preparation method and an application thereof. In the formula I, R1 is alkyl with 8-16 carbon atoms. The invention also further provides a preparation method of the thiol spirothiopyran compound, which comprises the following steps of: (1) carrying out cyclization on N-substituted indole shown in the formula II and o-aldehyde group para-nitrobenzene thiophenol to obtain N-alkyl bromide spirothiopyran shown in the formula III; and (2) under an acidic condition, nucleophilic substitution is carried out on the N-alkyl bromide spirothiopyran shown in the formula III and sulfo-potassium acetate to obtain the thiol spirothiopyran compound shown in the formula I. The invention provides an application of an electrode surface self-assembly layer made of the thiol spirothiopyran compound in preparing a functional organic photoelectric device, and the device is a good photoelectric functional organic semiconductor field effect transistor device. Under an ultraviolet irradiation condition, the working current of the device can be increased, and under a visual light irradiation condition, the working current of the device can be reduced. The thiol spirothiopyran compound has an important application value in the fields of photoelectric response sensors and high-density optical storage.
Description
technical field [0001] The invention relates to a mercaptospirothiopyran compound and its preparation method and application. Background technique [0002] Since the invention of the organic field effect transistor (OFET) in 1986 (Tsumura, A.; Koezuka, H.; Ando, T.Appl.Phys.Lett.1986, 49, 1210), due to its application in sensors, radio frequency tags, electronic paper , active matrix display and other directions have great potential application value, and thus have received widespread attention. In addition to improving OFET performance and optimizing device structure, the preparation of multifunctional optoelectronic OFET devices is also an important development direction in the field of organic electronics. In the past ten years, functional organic field effect transistors (FOFETs) have shown great application prospects and achieved considerable development in the fields of light detection, signal storage, laser emission, environmental monitoring, and drug delivery, and...
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