I Have a Research Support System

Xu Qiu's experiment today is about the reaction of aldehyde groups on IDTT and FN units. Wu Shengnan didn't come to Zhangjiang because of the submission of the article, so Xu just helped her to do the FN system. There are only two of the post-doctoral fellows.

Strictly speaking, this is the first time he has done this step of aldehyde reaction, but similar reactions have been carried out a lot, and with the experience gained from the senior sister, it must not be very difficult to vote. .

Xu Qiu first walked to the ten-liter liquid nitrogen container, opened the lid on the top of the container, and probed inside with a spoon hanging on the edge, estimating the amount of residual liquid nitrogen inside. There was about 30% to 40% of the returned liquid nitrogen, and there was no light leakage. It was enough for this reaction, and the reaction was started directly.

Redistill the THF solvent to obtain anhydrous THF;

Dissolving the IDTT/FN material in anhydrous THF;

Under the protection of nitrogen, the reaction vessel was cooled to minus 78 degrees Celsius with liquid nitrogen and maintained for 5 minutes;

Add n-butyllithium solution in the reaction vessel with a syringe;

Stirring was continued for one hour at -78°C, followed by the addition of anhydrous DMF by syringe.

The low temperature was no longer maintained, and the reaction vessel was allowed to slowly return to room temperature and stirred overnight.

Xu Qiu successfully submitted two reactions, and the target products were IDTT-CHO and FN-CHO.

At the same time, Xuemei also completed her two reactions, and the target products were H31 and H32.

The two returned to the A501 office next door. Xu Qiu walked to the sink and began to wash his hands. He glanced at the location of the mobile phone out of the corner of his eye and found that the breathing light was blinking, indicating that there was new news.

Speaking of which, the counselor has notified many things in succession recently, including the matter of obtaining graduation and degree certificates:

"Now the department is conducting a graduation review, and the graduation certificate will be issued around the beginning of July. If there are compulsory courses in this semester, and the grades are not issued before the graduation certificate is uniformly issued by the department, or the grades are passed, it will need to be delayed until September to issue the grades. Or pass the make-up exam to get the certificate."

The counselor didn't say anything about the consequences of failing to pass the make-up exam, but after thinking about it, I know that it will probably be delayed for half a year...

There is also the matter of the graduation ceremony: "At the end of June, the school will hold a graduation ceremony. At that time, bachelor uniforms will be distributed for photo taking; after the ceremony, the principal will pick ears for the students on the stage, and there will be activities to take pictures with the principal. If you are interested, please apply to the monitor of the class..."

What is it this time?

After Xu Qiu washed his hands, he picked up his phone and found that it was a message sent by the class leader in the class notification group.

"@Everyone class plans to organize a graduation red carpet event. The event time will be next Tuesday afternoon. The venue will be the Crowne Plaza Hotel next to the school. The fee will be about 100 yuan per person, including the shared venue rental fee and an afternoon tea buffet. The form is voluntary participation, this may be the last group activity of our graduating class, I hope everyone actively participates, interested students private message me to sign up..."

Xu Qiu has heard of such things as walking the red carpet after graduation. In fact, it was originally a special event of the Department of Journalism of Shanghai Comprehensive University. Since 2000, the Department of Journalism has been organizing red carpet activities for graduation. The specifications are different. Low, everyone dressed up to go out, the implication is generally to pay tribute to the beautiful university life in a beautiful way.

Among them, some alumni and celebrities from earlier years will also be invited to participate. After all, Shanghai University has a lot of influence in Shanghai's news circle. Many important people are from Shanghai University. I will forget my alma mater, and participating in such activities can also expand and stabilize my network through the alumni association, and achieve a win-win situation. Why not do it.

Over the years, this activity has gradually been followed by other departments and has gradually expanded to all departments of the school.

However, like the red carpet activities organized by the Department of Materials, the style of painting is not as exaggerated as that of the Department of Journalism. A thought or something.

It is a bit similar to Xu Qiuchu's classmate records written in high school. The students who have lived together in the university for four years have left some common memories with each other.

Compared with Classmates, walking the red carpet just looks more advanced, and there are not many essential differences.

The head of the material department booked the Crowne Plaza Hotel next to the school. The location is very good. This hotel is built between the south area of ​​the Shanghai University of Technology and the only way to the headquarters. It is said to be a five-star hotel. The room rate at night is a few hundred more, and if it is more expensive, it is almost a thousand.

Now the red carpet event is just renting a hall as a venue, and it is also a group event, so it is not expensive to share it equally.

Xu Qiu wasn't very interested in this kind of group activity at first, but he looked at the school girl next to him and asked for her opinion: "The class organizes a graduation red carpet event, do you think you want to go?"

"Go ahead, why not?" Han Jiaying took it for granted, "After all, we are classmates for three years."

"Then I'll sign up." Xu Qiu paused, and suddenly said: "This kind of event usually involves family members, will you join me too?"

Han Jiaying twitched for a while, then said in a whisper, "Mmm~"

In the evening, Han Jiaying began to process her reaction, which only took four hours to complete because a microwave reactor was used for this reaction.

There are two reactions in total, each of Xu Qiu and Xuemei are treated separately. First, the reaction solution is dropped into methanol to precipitate polymers, filtered, and vacuum-dried. Then, a Soxhlet extraction device is set up and cleaned with methanol, acetone, and n-hexane. .

With the enrichment of experimental experience and the use of microwave reactors, the polymerization reaction used to take a week, but now it only takes two or three days to get the final product.

On Tuesday, Wu Shengnan had already rejected her article on electrofluorescence discoloration, and Chen Wanqing had completed the characterization data of the IEIC system, so the two of them also went to Zhangjiang with Xu Qiu and Han Jiaying.

So much so that when Mr. Wei went to the office in the morning, he found that Duan Yun was the only one in room 216.

"Where are the others?" Wei Xingsi asked.

Duan Yun was also confused, but he still replied: "Wu Feifei should have gone to class, Tian Qing doesn't know, Xu Qiu and the others probably went to Zhangjiang?"

"Okay." Teacher Wei nodded and thought about it carefully, "Wu Feifei is now considered to be a first-year Ph.D. student, and she needs to take more than ten credits of courses for her master's and doctoral degree. It seems that there is a class today. Tian Qing will give it to me in the morning." I sent a message saying that I'm not feeling well and I have to come later, maybe in the afternoon, Xu Qiu and the others... I'll give him a call later. '

So, when Xu Qiu was preparing for the experiment, he received a call from Teacher Wei, who said, "Everyone else is here", and asked them to call each other a few times. Teacher Wei told them to "be careful", and then Hang up the phone.

It's just a pain for Duan Yun, he was found by Teacher Wei four times throughout the morning, and whenever Wei Xingsi passed the 216 office, he would go in to see what Duan Yun was doing.

In Zhang Jiang's laboratory, Han Jiaying handled the Soxhlet extraction devices of her two products, H31 and H32, and switched the extraction solution to chloroform for extraction again.

Chen Wanqing started the synthesis of IEICO and IEICS. IDT and ICIN units are in stock. She only needs to synthesize thiophene (T) units with different side chains in the center, but the reaction steps are slightly longer. To obtain the final product, a total of five step reaction, and two of them are new reactions, and one reaction is a low-temperature reaction of n-butyllithium, which is estimated to take more than a week to synthesize.

Xu Qiu and Wu Shengnan will carry out the last step of the reaction of ADA-type non-fullerene acceptor materials, that is, the reaction of the aldylated D unit and the A unit to form the ADA structure.

This step requires the use of pyridine...

The seniors were using it before, and now it's finally their turn.

In order not to affect other people's normal experiments, Xu Qiu and Wu Shengnan could only start experiments at night.

They also have something to do during the day, which is to post-process yesterday's reaction, first extract it with dichloromethane, then wash it with water, dry it, and mix the sample.

The previous batch of disposable silica gel columns had been reused many times, and there were fewer and fewer clean columns. Xu Qiu gave up after choosing for a long time.

Therefore, they chose to fill in the pillars by hand this time. Xu Qiu and Wu Shengnan spent more than ten minutes "duang" and "duang" beside the fume hood, and finally filled the two pillars.

The following column operation is not difficult, and the petroleum ether/dichloromethane system is still used, because the molecular structures of the materials they synthesized are relatively similar, and the main part is a large conjugated fused ring structure, and the polarity changes not big.

In the evening, both the seniors and the juniors finished their responses, and the laboratory was vacated, which became the stage for Xu Qiu and Wu Shengnan.

The two of them put on gas masks, protective clothing and three-layer gloves, opened the windows for ventilation, and made sufficient preparations before taking out the pyridine reagent from the reagent cabinet and starting the reaction.

There are three kinds of acceptor units synthesized this time, which are ICIN-2F/2Cl/DM, and two kinds of donor units IDTT and FN. If the initial donor unit IDT and an acceptor are added Unit ICIN, that is four A units, three D units, if combined in pairs, there are a total of 12 possibilities for change.

Naturally, Xu Qiu and the others cannot cast 12 responses at once. On the one hand, their strength does not allow it; One is a new unit, so that the performance of the final device has improved or decreased, which is easier to analyze.

In the end, Xu Qiu decided to synthesize three structures of IDTT-ICIN, IDT-ICIN-4F, and IDT-ICIN-4Cl for the first reaction, while Wu Shengnan had two structures of FN-ICIN and IDT-ICIN-DM.

Start experimenting.

First, weigh the aldylated D unit and A unit separately. After the last step of the reaction, you can directly get the final ADA material. You don’t need to synthesize a lot like before, as long as you get 100-200 mg of product, it’s enough. That's fine.

Next, dissolve the formylated units D and A with 30 ml of chloroform solvent, then add 1 ml of pyridine, and connect a nitrogen balloon to provide a nitrogen protective atmosphere.

Finally, the reaction vessel was placed in an oil bath at 70° C., heated and stirred under reflux for 15 hours. (When the heating temperature exceeds the boiling point of the solvent, the liquid solvent in the reaction vessel will boil, and part of the liquid molecules will be converted into gaseous solvent molecules, and the gaseous solvent molecules will move upwards, be cooled to a liquid state at the condenser tube, and flow back into the reaction vessel. The process is called reflow.)

After five responses were cast, Xu Qiu and Wu Shengnan continued to wear gas masks, checked around the laboratory, and then closed the laboratory with the fume hood open.

It has to be said that the effect of the gas mask is indeed very powerful. Before wearing it, Xu Qiu could not smell any peculiar smell at all. Now when he was walking at the door of the laboratory, he just took off the mask, and he smelled a faint The smell of pyridine.

Xu Qiu and Wu Shengnan blew the hot summer air in the ventilation area for more than ten minutes before returning to the A501 office.

On Wednesday, the organic quartet gathered in Zhangjiang again.

Xu Qiu and Wu Shengnan were post-processing the five responses from yesterday.

Because the pyridine used is not the main solvent, only 1 ml was added to each reaction, so it is not very troublesome to handle. The product is directly poured into 200 ml of methanol, and the small molecule ADA product is precipitated, then filtered, dried, and then re- Dissolve, mix the sample, pass through the column, and add a small amount of hydrochloric acid to the methanol waste liquid containing pyridine for treatment.

It takes about one to two hours to pass a pillar, plus the time for lunch and dinner in the middle, Xu Qiu and Wu Shengnan worked until after 8 o'clock in the evening, and finally got five ADA types of non-fullerene receptors. All in 100-200 mg.

Xuemei also obtained her H31 and H32 products by rotary evaporating chloroform solvent, dropping methanol, filtering, and vacuum drying.

Among the four, only the senior has not yet obtained the final product, and her reaction is still in progress. There are a total of five steps in the reaction, and now only two steps have been completed.

Xu Qiu brought five products back to Handan along with two products of his classmates, and copied them to the simulation laboratory at the same time, and arranged for simulation experimenters to start testing the device performance.

Although the time ratio of simulation lab II to reality is 1:1, as long as the points are enough, the simulation experimenters can work day and night, and there are two people in total. For this kind of repetitive work, the efficiency is sure. It is far beyond Xu Qiu's experiment in reality.

Therefore, Xu Qiu also assigned the second priority to the simulation experimenters, asking them to synthesize seven other ADA non-fullerene acceptor materials.

The time to test the results has finally arrived.