Chapter 301: The time to test the results has finally arrived

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The content of Xu Qiu’s experiment today is the reaction of the aldehyde groups on the IDTT and FN units. Wu Shengnan didn’t come to Zhang Jiang because of the article, so Xu directly helped her make the FN system. Anyway, today’s experiment is not under pressure. After going to the Ph.D. there are only two seniors.
Strictly speaking, this step of the aldehyde grouping reaction is the first time he has done it, but similar reactions have been done a lot, plus the experience gained from the school 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 container, and probed inside with a spoon hanging on the edge, and estimated the amount of residual liquid nitrogen inside. After some investigation, he judged that the school girl last week The liquid nitrogen returned was about 30-40% remaining, and it did not leak completely. It was enough for this reaction, and the reaction started directly.
Re-evaporate the THF solvent to obtain anhydrous THF;
Dissolve IDTTFN material in anhydrous THF;
Under the protection of nitrogen, use liquid nitrogen to cool the reaction vessel to minus 78 degrees Celsius for 5 minutes;
Use a syringe to add n-butyl lithium solution to the reaction vessel;
Continue stirring at minus 78 degrees Celsius for one hour, and then add anhydrous DMF with a syringe.
The low temperature is no longer maintained, and the reaction vessel is slowly returned to room temperature and stirred overnight.
Xu Qiu successfully completed two reactions, and the target products were IDTT-CHO and FN-CHO.
At the same time, the school girl also completed her two reactions, the target products were H31 and H32.
The two returned to the nearby A501 office. Xu Qiu walked to the sink and began to wash his hands. He glanced at the location of the phone from the corner of his eye and found that the breathing light was flashing, indicating that there was new news.
Speaking of, the counselor has recently notified a lot of things, including graduation and degree certificates:
"The department is currently undergoing a graduation review. The graduation certificate will be issued around the beginning of July. If there are compulsory courses in this semester, and the department has no grades before the uniform issuance of the graduation certificate, or the department fails, it needs to be delayed until September. Or pass the make-up exam to get the certificate."
The instructor did not say about the consequences of failing to pass the make-up exam at the time, but after thinking about it, I know that it will probably be postponed for six months...
There is also a graduation ceremony: "At the end of June, the school will hold a graduation ceremony. At that time, bachelor uniforms will be handed out for taking pictures. After the ceremony, the principal will pick up the ears for the students on stage and take photos with the principal. , Those who are interested find the monitor to sign up..."
What happened this time?
After Xu Qiu washed his hands, picked up his mobile phone and found that it was a message sent by the supervisor in the class notification group.
"@人民班级计划 organizes a graduation walk on the red carpet. The activity time is next Tuesday afternoon at the Crowne Plaza Hotel next to the school. The charge is about 100 yuan per person, including an evenly shared venue rental fee and an afternoon tea buffet. The form of participation is voluntary. This may be the last group activity for our graduating class. I hope everyone will participate actively. Interested students will chat privately with me to sign up..."
Xu Qiu has heard of things like going to graduate and walking on the red carpet. In fact, it was originally a special event of the Journalism Department of Madu Comprehensive University. About a few years ago, the Department of Journalism began to organize graduation activities on the red carpet. Low, everyone dressed up to travel, the implication is roughly a tribute to the beautiful university life.
Among them, some early alumni and celebrities will also be invited to participate. After all, the influence of Mordu Comprehensive University in the press is not small. Many important figures are from the Mordu Comprehensive University, and they will naturally not become famous. 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 been gradually followed by other faculties and departments, and has gradually expanded to all faculties of the school.
However, for example, the materials department organizes red carpet activities. The style of painting is not as ostentatious as the journalism department. It is relatively pure. Generally, it is to bring family members, or be alone, walk on the red carpet, and take pictures with good classmates. A thought or something.
It's a bit similar to the classmates Xu Qiuchu wrote in high school. The students who spent four years in the university left some common memories with each other.
Compared with classmates, walking the red carpet just looks more advanced, and there is not much essential difference.
The head of the Department of Materials booked the location at the Crowne Plaza Hotel next to the school. The location is very good. This hotel is built between the southern area of ​​the Magic University 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 higher, and if it’s more expensive, it’s almost a thousand.
Now the red carpet activities are just renting a hall as a venue, and it is also a group activity, so it is not expensive to share it.
Xu Qiu was not very interested in this kind of group activities, but he looked at the school girl next to him and asked her for her opinion: "The class organizes graduation red carpet activities, do you want to go?"
"Go, why not?" Han Jiaying took it for granted: "How do you say it's a three-year classmate."
"Then I will sign up." Xu Qiu paused, and suddenly said, "This kind of activity usually involves bringing family members. Are you with me too?"
Han Jiaying squeezed for a while, and said, "Hmm~"
In the evening, Han Jiaying started to deal with her reaction. Because this reaction used a microwave reactor, it only took four hours to complete.
There are two reactions in total, Xu Qiu and Xuemei, one by one, and they are processed separately. First, the reaction solution is dropped into methanol to precipitate the polymer, filtered, and vacuum dried. Then, a Soxhlet extraction device is set up and washed with methanol, acetone, and n-hexane. .
With the enrichment of experimental experience and the use of microwave reactors, the polymerization reaction originally took one week, but now it only takes two or three days to obtain the final product.
On Tuesday, Wu Shengnan had already submitted her article on electroluminescence color changes, and the characterization data of Chen Wanqing's IEIC system was also completed, so the two of them also went to Zhangjiang with Xu Qiu and Han Jiaying.
So when Teacher Wei arrived at the office in the morning, he found that there was only Duan Yun in Room 216.
"Where are the others?" Wei Xingsi asked.
Duan Yun was also dumbfounded, but still replied: "Wu Feifei should have gone to class, Tian Qing is not sure, Xu Qiu and the others are going to Zhangjiang?"
"Okay." Teacher Wei nodded and thought about it carefully, "Wu Feifei is now regarded as the first year of Ph.D., and she has to take more than a dozen credits for continuous master and doctor. It seems that there is a class today. Tian Qing gave me this morning. I sent a message saying that I was feeling sick and I had to come here later, maybe in the afternoon, Xu Qiu and the others... I'll call him later. ’
Therefore, when Xu Qiu was preparing for the experiment, he received a call from Teacher Wei and said that "the others are here" and asked them to call each other a few times. Teacher Wei urged him to "pay attention to safety". Hung up the phone.
Duan Yun just suffered. He was found by Teacher Wei four times throughout the morning. Whenever Wei Xingsi went to the 216 office, he would go in to see what Duan Yun was doing.
At Zhang Jiang’s laboratory, Han Jiaying handled the Soxhlet extraction device for her two products, H31 and H32, and switched the extraction solution to chloroform to perform extraction again.
Chen Wanqing started to synthesize IEICS. IDT and ICIN units are in stock. She only needs to synthesize thiophene (T) units with different side chains in the center. The reaction steps are slightly longer. To obtain the final product, a total of five steps are required. The reaction, and two of them are new reactions, one is the low-temperature reaction of n-butyllithium, and it is estimated that it will take more than one week to synthesize.
Xu Qiu and Wu Shengnan need to perform the final reaction of the ADA-type non-fullerene acceptor material, that is, the reaction between the aldehyde-based D unit and the A unit to form an ADA structure.
This step requires pyridine...
They were all using it before, but now it's their turn.
In order not to affect other people's normal experiments, Xu Qiu and Wu Shengnan could only start the experiment at night.
They also have something to do during the day, that is, to post-process yesterday's reaction, first extract with dichloromethane, then wash with water, dry, and mix samples.
The previous batch of disposable silica gel columns was reused many times, and there were fewer and fewer relatively clean columns. Xu Qiu gave up after picking it for a long time.
Therefore, they chose to fill the columns manually this time. Xu Qiu and Wu Shengnan "duang" and "duang" by the fume hood for more than ten minutes, and finally filled the two columns.
The next column operation is not difficult, the petroleum ether dichloromethane system is still used, because the molecular structure of the materials synthesized by them is relatively similar, the main part is a large conjugated fused ring structure, and the polarity change is not Big.
In the evening, both the school sister and the school girl completed their reactions, and the laboratory was vacated and became the stage for Xu Qiu and Wu Shengnan.
The two of them put on gas masks, protective clothing and three layers of gloves, opened the window for ventilation, and made enough preparations. Then they took out the pyridine reagent from the reagent cabinet and started to react.
There are three types of acceptor units synthesized this time, namely ICIN-2F2ClDM, and two donor units IDTT and FN. If you add the initial donor unit IDT and the acceptor unit ICIN, then There are four types of A units and three types of D units. If you combine them in pairs, there are a total of 12 possible changes.
Naturally, it is impossible for Xu Qiu and the others to cast 12 responses at once. On the one hand, their strength is not allowed. On the other hand, in this exploratory research process, they usually use the controlled variable method. One is a new unit, so that the final device performance is improved or reduced, and it is easier to analyze.
In the end, Xu Qiu decided to synthesize IDTT-ICIN, IDT-ICIN-4F and IDT-ICIN-4Cl for the first time, and Wu Shengnan had FN-ICIN and IDT-ICIN-DM.
Start the experiment.
Firstly, weigh the aldehyde-based D unit and A unit separately. The final step of the reaction is achieved, and the final ADA material can be obtained directly. There is no need to synthesize a lot like before, as long as 100-200 mg of product is obtained, which is enough That's it.
Next, use 30 ml of chloroform solvent to dissolve the aldehyde-based D unit and A unit, then add 1 ml of pyridine, and connect to a nitrogen balloon to provide a nitrogen atmosphere.
Finally, the reaction vessel was placed in an oil bath at 70 degrees Celsius, and heated and stirred to 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 some liquid molecules will be converted into gaseous solvent molecules. The gaseous solvent molecules move upwards, are cooled to liquid at the condenser tube, and flow back to the reaction vessel. Backflow.)
After the five reactions were completed, Xu Qiu and Wu Shengnan continued to wear gas masks and inspected the laboratory for a round, then kept the fume hood normally open and shut down the laboratory.
I have to say that the effect of the gas mask is indeed very powerful. When he was wearing it before, Xu Qiu could not smell any peculiar smell at all. Now walking at the door of the laboratory, he just took off the mask and he smelled a faint smell. The smell of pyridine.
Xu Qiu and Wu Shengnan blew the hot summer wind for more than ten minutes in the ventilating place before returning to the A501 office.
On Wednesday, the organic group of four gathered in Zhang Jiang again.
Xu Qiu and Wu Shengnan performed post-processing of five reactions yesterday.
Because the pyridine used is not the main solvent, only 1 ml is added for each reaction, so it is not very troublesome to handle. Pour the product directly into 200 ml of methanol. The small molecule ADA product is precipitated, then filtered, dried, and then renewed. Dissolve, mix the sample, pass 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 column. In addition to the mid-course meal and dinner time, Xu Qiu and Wu Shengnan worked hard until more than eight o'clock in the evening, and finally received five ADA types of non-fullerene receptors. Both are 100-200 mg.
Xuemei also obtained her H31 and H32 products by rotating the chloroform solvent, dripping methanol, filtering, and vacuum drying ~EbookFREE.me~.
Among the four, only the senior sister has not received the final product. Her reaction is still in progress. There are five steps in the reaction, and now only two steps have been completed.
Xu Qiu brought the five products back to Handan along with the two products of Xuemei, and copied them to the simulation laboratory at the same time, and arranged for simulation experimenters to start the device performance test.
Although the time ratio of Simulation Lab II to reality is 1:1, as long as the points are sufficient, the simulation experimenters can work day and night, and there are two people in total. For this kind of repetitive work, the efficiency is certain It is far beyond Xu Qiu to experiment in reality.
Therefore, Xu Qiu also arranged the second priority work for the simulation experimenters, and asked them to synthesize another seven ADA non-fullerene acceptor materials.
It's finally time to test the results.
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