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Bis(dithio hydrocarbon)-2,5-bis(1,3-dithiol-2-ylidene)-1,3,4,6-tetrathiapentalene (TTP) organic conductive crystal and preparation method thereof

A technology of fullvalene type and bis-disulfide, applied in the field of bis-disulfide-double-fused tetrathiafulvalene type organic conductive crystal and its preparation

Inactive Publication Date: 2014-11-05
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, strong intermolecular S...S interactions link electrical conductivity with poor solubility, making the solubility problem a bottleneck for the development of organic conductive crystals.

Method used

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  • Bis(dithio hydrocarbon)-2,5-bis(1,3-dithiol-2-ylidene)-1,3,4,6-tetrathiapentalene (TTP) organic conductive crystal and preparation method thereof
  • Bis(dithio hydrocarbon)-2,5-bis(1,3-dithiol-2-ylidene)-1,3,4,6-tetrathiapentalene (TTP) organic conductive crystal and preparation method thereof
  • Bis(dithio hydrocarbon)-2,5-bis(1,3-dithiol-2-ylidene)-1,3,4,6-tetrathiapentalene (TTP) organic conductive crystal and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Embodiment 1, double disulfide vinylidene-double fused tetrathiafulvalene (BV-TTP)

[0072] The synthetic route shows:

[0073]

[0074] 0.089g (0.40mmol) of the small precursor compound was placed in a 50mL three-necked round-bottomed flask, and the nitrogen gas was pumped and changed 3 times. Under the protection of dry nitrogen, add 10mL of freshly steamed toluene, heat and stir until completely dissolved, and naturally cool to 50°C; add 0.101g (0.26mmol) of the large precursor compound to the above solution, and immediately add 7mL of freshly steamed coupling agent with a syringe P(OMe) 3 , pump and change nitrogen 3 times; accelerate stirring, heat up to 108°C, start to boil, reflux under nitrogen for 20 hours, cool naturally, then put in refrigerator -10°C overnight, then add 5mL of methanol, filter and dry to get reddish brown Crude solid 0.094 g. Filtrate dot plate (carbon disulfide as developing agent) found: there is a small precursor compound, indicatin...

Embodiment 2

[0088] Embodiment 2, double disulfide ethylene-double fused tetrathiafulvalene (BE-TTP)

[0089] The synthetic route shows:

[0090]

[0091] Preparation method is as embodiment 1, and difference is:

[0092] The reactants were: 0.088g (0.39mmol) of the small precursor compound, 0.103g (0.27mmol) of the large precursor compound, the reflux time was 22 hours under nitrogen, and 0.077g of a reddish-brown solid was obtained after suction filtration and drying. The filtrate was plated, and no small precursor compounds were found.

[0093] The reddish-brown solid was placed in a Soxhlet extractor for the first 5-day extraction with carbon disulfide. The extract is separated by column chromatography. First, the redistilled dichloromethane is used as the eluent to elute the self-conjugate BE-TTF of the small precursor compound (see the background technology part for the structural formula); then carbon disulfide is used as the eluent , the obtained eluate was slowly concentrate...

Embodiment 3

[0102] Example 3, disulfide ethylene-disulfide methylene-double fused tetrathiafulvalene (EM-TTP)

[0103] The synthetic route shows:

[0104]

[0105] Preparation method is as embodiment 1, and difference is:

[0106] The reactants were: 0.087g (0.41mmol) of the small precursor compound and 0.104g (0.27mmol) of the large precursor compound. After 18 hours of reaction, they were placed in the refrigerator overnight to obtain 0.049g of a reddish-brown solid. The filtrate was plated, and no small precursor compounds were found.

[0107]The above solid was placed in a Soxhlet extractor, and the first extraction was carried out with carbon disulfide for a period of 5 days. The extract was separated by column chromatography, and the self-conjugate BM-TTF (structural formula is as follows) of the small precursor was eluted with redistilled dichloromethane as the eluent; then carbon disulfide was used as the eluent to elute the corresponding After dehydration and slow concentra...

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Abstract

The invention provides a bis(dithio hydrocarbon)-2,5-bis(1,3-dithiol-2-ylidene)-1,3,4,6-tetrathiapentalene (TTP) organic conductive crystal and a preparation method thereof. The crystal has the structure shown in formula I, and includes BV (bis(vinyl dithio))-TTP crystal, BE (bis(ethyl dithio))-TTP crystal, EM (bis(ethyl dithio)) (bis(methyl dithio))-TTP crystal and EV (bis(ethyl dithio)) (bis(vinyl dithio)-TTP crystal. The electrical conductivity along the crystal long axis direction of the BE-TTP crystal, the EM-TTP crystal and the EV-TTP crystal is greater than 1*10<-3> Omega<-1>cm<-1>. The preparation method comprises (1) in a particular feeding sequence and ratio and nitrogen conditions, first, a small precursor compound is dissolved in toluene, then a large precursor compound is added, finally coupling agent P (OMe) 3 is added, the molar ratio of the small precursor compound to the large precursor compound is 1.5-2:1; and (2) by a method of combination of extraction and column chromatography, then secondary extraction and crystallization, the product is purified to obtain a high pure crystal. An improved Soxhlet extractor is used for extraction, and high purity carbon disulfide is used for extraction for long time in oxygen-free water-free lucifugal closed conditions. The four organic crystals of the BV-TTP crystal, the BE-TTP crystal, the EM-TTP crystal and the EV-TTP crystal are artificially synthesized single element organic conductive crystals, and corresponding four compounds have important practical significance in semiconductors and electrode materials and other aspects.

Description

technical field [0001] The invention relates to a sulfur-rich bisdisulfide-bis-fused tetrathiafulvalene type organic conductive crystal and a preparation method thereof, belonging to the technical field of organic functional materials. Background technique [0002] Organic solids are generally insulators. The rise of organic conductors in the 1960s has greatly enriched and deepened people's understanding of the structure of crystalline substances, and directly promoted the development of organic photoelectric functional materials, in semiconductor materials, photoelectric conversion materials, sensing materials, electrode materials, information storage and so on show broad application prospects. The main feature of organic conductive materials is diversity, which can be compatible with plastic electronics and bioelectronics, and also connect with future molecular electronic devices. [0003] Organic conductive crystals are crystalline organic conductors, which are crystals...

Claims

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Application Information

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IPC IPC(8): C07D519/00H01L51/30
CPCC07D519/00H10K85/655H10K85/6576
Inventor 方奇陈红凤薛刚
Owner SHANDONG UNIV
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