Now we can finally play rock paper scissors. Cherry flavouring beats paint thinner Glowing dye beats cherry flavoring And finally paint thinner beats glowing dye
I work as a junior histologist performing immunofluorescent imaging in the US- I’m very glad you made a video on this, the composition of most dyes my lab buys are proprietary so I can’t read and obsess about them 😢 All of them have a (similarly to BNAX) planar molecular geometry. These dyes remain fluorescently inactive until bound to electron donating moeities on specific proteins within the sample- most of the ones we use rely on radical substitution to form localized hydroxyl radicals, which then proliferate to form “tyramide” (dye) radicals- these bind to protein residue and once bound fluoresce, exhibiting a characteristic excitation and emission wavelength. A fluorescent dye I’ve been meaning to look into is hoechst 33342, it’s one of many (collectively referred to as DAPI) that are used to stain the nuclei of cell sections mounted on microscope slides. Just thought you might find some of this interesting, thank you for the videos!
Did you notice the non-fluoresent blue/purple vial with water? Since the molecule is relatively planar, I would imagine this is some sort of dimer formation or pi-pi stacking occuring which is quenching fluorescence.
Hey, nice that you have done the synthesis and made a video about it. I'm the author of the post from the German forum and this is probably one of my favorite molecules, just because of the overlap of an interesting structure, fascinating properties and the relatively easy accessibility. After I dug up the synthesis and gave it a try, it also became one of the multi-step standard preparations in the lower OC practical courses at my university, because of those very characteristics and reproducibility. A friend also told me that the crystallization of the xanthylium bromide did not work for him, or that no crystals formed at all, but in my 4 attempts (3 times with the xanthylium bromide from benzaldehyde and once with it from 4-bromobenzaldehyde) I always had a consistently acceptable yield with successful crystallization. Unfortunately, I don't know why it doesn't seem to work sometimes. In the photocatalytic Scholl-type didehydrogenation, no H2 is formed but H2O, which comes from (the for this reaction in stochiometric quantities needed) oxygen dissolved in the solvent; while the starting material is readily soluble in acetonitrile, the product precipitates as fine needles. According to the literature, the reaction can also be carried out in glacial acetic acid, but this seems too cumbersome. The concentration in which you carried out the reaction was probably too high. Diluted solutions work better (that's why HOAc sucks). Solutions of the xanthylium bromide are photochemically unstable because the BNAX is favoured. The xanthylium bromide shows a green fluorescence in solution witch turns yellow to orange within a few seconds under UV light, so the photoreaction is very fast. Maybe due to too much light during the reaction/crystallization the xanthylium bromide produces BNAX and there is no further crystallization?! The BNAX-PF6 salt is also insoluble in acetonitrile and precipitates (once precipitated it with NH4PF6). As far as I remember, it is not suitable as a dye for glow sticks - but this is not surprising: the dye is too reactive due to its xanthylium structure and is sensitive to reactive substances, presumably oxidizing agents. The solutions are also not photostable in direct sunlight and change both their color and fluorescence. I have not even tried that the product is soluble in water, thanks for the note about solvtochromism! :) The two analogues with sulfur and nitrogen (as phenylacridinium) are also described in literature, but both are less interesting: both the colors and the fluorescence are visually less appealing and the effort, at least for the sulfur analogue, is higher. Go on with your work! :D Kind regards NI2
7:23 actually KFC don't use deep friers, they use PRESSURE friers. It's some scary shit, but the only way to get it cooked well and retain all that moisture xD
Fluorescent dyes and materials make me so happy, and I'm not entirely sure why. Just love how vivid they are backed by that deep purple or blue UV. Also, the structure of that BNAX molecule pleases me. 😎
I've worked on similar compounds - they are very potent dyes and they tend to form metallic crystals. Try making the BF4- salt and crystallising them for some very cool crystals.
Son: Why is my sister called Roma? Dad: Because we were in Italy when she was born. Son: Thanks Dad Dad: You're welcome, 14-Phenyl-14H-dibenzo[a,j]xanthene
7:08 just a quick note, you should use a ball condenser wether water or air cooled doesn't matter for a reflux, but you shouldn't use a straight condenser vertically, as convection can allow volatile molecules to not touch the sides and escape
There is an alternate reaction to get the second product using acetic anhydride, lead dioxide and then reacting the product with azeotropic hydrobromic acid to get the bromide salt.
Boys and girls of every age Wouldn't you like to see something strange? Come with us and you will see This, our town of Halloween This is Halloween, this is Halloween Pumpkins scream in the dead of night This is Halloween, everybody make a scene Trick or treat 'til the neighbors gonna die of fright It's our town, everybody scream In this town of Halloween
pH indicators? Not only are they colorful, they also vary in color depending on their chemical environment, so they can be useful for inorganic chemistry purposes
6:35 I can also attest to 2-napthol smelling really bad, I once made the mistake of grinding it in a mortar and pestle, and even after cleaning it, I could smell it weeks later
Ah, yes, the branch of the craziest element on the periodic table and how it bonds to itself or hydrogen. It's a literal sandbox, anything, no matter how crazy it sounds (should be) is possible Edit: I'm gonna get ahead of the comments about tar and say, if you do, I'll report you without thinking twice
Why did you need to wait for it to cool? Couldn't you have filtered it when the desired crystals appeared while hot? That way they don't have the potential to be over-brominated while the reaction continues. Then you could just repeat the process with the filtrate until you're happy with the yield.
Sounds like you have an inverse solubility problem with trying to get your crystals. Hot filtering might work. Edit: no idea why it didn't recrystalize when heated for distillation.
paint thiner to cherry flavoring, cherry flavoring to glowing dye
Journey (may be) complete
Made possible by chemistry.
I love chem
Now we can finally play rock paper scissors.
Cherry flavouring beats paint thinner
Glowing dye beats cherry flavoring
And finally paint thinner beats glowing dye
Glowing dye to demon core.
0:23 Incorrect. Organic chemistry focuses mainly on tar and its various forms.
And even the feared YELLOW chemistry
Virgin primary official peer reviewed sources vs Chad amateur chemist forum recipes.
original paper from 2009: DOI 10.1021/ol902366y
I work as a junior histologist performing immunofluorescent imaging in the US- I’m very glad you made a video on this, the composition of most dyes my lab buys are proprietary so I can’t read and obsess about them 😢
All of them have a (similarly to BNAX) planar molecular geometry. These dyes remain fluorescently inactive until bound to electron donating moeities on specific proteins within the sample- most of the ones we use rely on radical substitution to form localized hydroxyl radicals, which then proliferate to form “tyramide” (dye) radicals- these bind to protein residue and once bound fluoresce, exhibiting a characteristic excitation and emission wavelength.
A fluorescent dye I’ve been meaning to look into is hoechst 33342, it’s one of many (collectively referred to as DAPI) that are used to stain the nuclei of cell sections mounted on microscope slides. Just thought you might find some of this interesting, thank you for the videos!
Did you notice the non-fluoresent blue/purple vial with water? Since the molecule is relatively planar, I would imagine this is some sort of dimer formation or pi-pi stacking occuring which is quenching fluorescence.
you know, the smarter someone is, the simpler they are able to describe a complex subject. you are genuinely such a genius!
Wouldn't it be awesome if you could make a Blue or Violet fluorescent dye THAT bright!
Hey, nice that you have done the synthesis and made a video about it. I'm the author of the post from the German forum and this is probably one of my favorite molecules, just because of the overlap of an interesting structure, fascinating properties and the relatively easy accessibility. After I dug up the synthesis and gave it a try, it also became one of the multi-step standard preparations in the lower OC practical courses at my university, because of those very characteristics and reproducibility.
A friend also told me that the crystallization of the xanthylium bromide did not work for him, or that no crystals formed at all, but in my 4 attempts (3 times with the xanthylium bromide from benzaldehyde and once with it from 4-bromobenzaldehyde) I always had a consistently acceptable yield with successful crystallization. Unfortunately, I don't know why it doesn't seem to work sometimes.
In the photocatalytic Scholl-type didehydrogenation, no H2 is formed but H2O, which comes from (the for this reaction in stochiometric quantities needed) oxygen dissolved in the solvent; while the starting material is readily soluble in acetonitrile, the product precipitates as fine needles. According to the literature, the reaction can also be carried out in glacial acetic acid, but this seems too cumbersome. The concentration in which you carried out the reaction was probably too high. Diluted solutions work better (that's why HOAc sucks). Solutions of the xanthylium bromide are photochemically unstable because the BNAX is favoured. The xanthylium bromide shows a green fluorescence in solution witch turns yellow to orange within a few seconds under UV light, so the photoreaction is very fast. Maybe due to too much light during the reaction/crystallization the xanthylium bromide produces BNAX and there is no further crystallization?!
The BNAX-PF6 salt is also insoluble in acetonitrile and precipitates (once precipitated it with NH4PF6).
As far as I remember, it is not suitable as a dye for glow sticks - but this is not surprising: the dye is too reactive due to its xanthylium structure and is sensitive to reactive substances, presumably oxidizing agents. The solutions are also not photostable in direct sunlight and change both their color and fluorescence.
I have not even tried that the product is soluble in water, thanks for the note about solvtochromism! :)
The two analogues with sulfur and nitrogen (as phenylacridinium) are also described in literature, but both are less interesting: both the colors and the fluorescence are visually less appealing and the effort, at least for the sulfur analogue, is higher.
Go on with your work! :D
Kind regards
NI2
7:23 actually KFC don't use deep friers, they use PRESSURE friers. It's some scary shit, but the only way to get it cooked well and retain all that moisture xD
Okay yeah, thats quite a fun color
"forbidden ice cream" made my day ngl
Personally, I got a good laugh out of the "reject the sun; embrace China" comment... 😂😂😂
13:07 Ah...that was painful, glad you didn't include the glass scratching sound as well, it would drive me crazy!
I LOL-ed at the “forbidden ice cream” remark around 14 minutes into the video
Fluorescent dyes and materials make me so happy, and I'm not entirely sure why. Just love how vivid they are backed by that deep purple or blue UV. Also, the structure of that BNAX molecule pleases me. 😎
Just wanted to say I love your sense of humor and the editing, the effort is appreciated
Amazing video ! You did a lot of hard work but the result !!!
Łelkam tu amaczur kemistri i dzień od razu lepszy 😊
Perfect !
You know it’s going to be good when it’s found on a German forum 😂
Richtig.😊
Yay more colorful chemistry
The man himself returns with more pretty colours and deep-fried chemistry 😊
Pozdro Ziom !!
Polska guromm! XD
Czesc Polska! (I don't have polish letters)
Polska mistrzem Świata!!!!
16:35 The Red Sun in the Sky 天上太阳红呀红通通 唉 👍
If NileRed was actually good^^
I've worked on similar compounds - they are very potent dyes and they tend to form metallic crystals. Try making the BF4- salt and crystallising them for some very cool crystals.
very kul mr polski
If your pee turns purple in the sun, go to the hospital.
Why I love the color purple!
Your channel is on my top 2
You're my favorite chemistry channel after nilered❤❤❤
You pronounced BNAX and my furniture started floating
Son: Why is my sister called Roma?
Dad: Because we were in Italy when she was born.
Son: Thanks Dad
Dad: You're welcome, 14-Phenyl-14H-dibenzo[a,j]xanthene
🤣😂🤣
YEEE NEW WIDEOOO
xanthene looks absolutely WILD as a molecule
If at 13:58 you imagine the flask with a transparent liquid with a crust on top you can get tripped out when he flips the flask
7:08 just a quick note, you should use a ball condenser wether water or air cooled doesn't matter for a reflux, but you shouldn't use a straight condenser vertically, as convection can allow volatile molecules to not touch the sides and escape
Very interesting :) good job!
7:05 Nice Transition
Ah, yes, being welcomed to a Mature Chemistry, love it.
Actually it is 3 branches, you forgot physical chemistry.
The molecule looks wild, I wonder if it's large... area? cross-section? is what makes it such a potent fluorescent dye
I was just looking at Coumarin dyes... ;)
I think a video on chlorine oxides would be great.
There is an alternate reaction to get the second product using acetic anhydride, lead dioxide and then reacting the product with azeotropic hydrobromic acid to get the bromide salt.
this is cool
Boys and girls of every age
Wouldn't you like to see something strange?
Come with us and you will see
This, our town of Halloween
This is Halloween, this is Halloween
Pumpkins scream in the dead of night
This is Halloween, everybody make a scene
Trick or treat 'til the neighbors gonna die of fright
It's our town, everybody scream
In this town of Halloween
Diphenyloxalate also works for making glowsticks
pH indicators? Not only are they colorful, they also vary in color depending on their chemical environment, so they can be useful for inorganic chemistry purposes
That was really cool! Could you use it to dye something like vegetable tan leather?
ayo i also use glassware from GLASSCO
6:35 I can also attest to 2-napthol smelling really bad, I once made the mistake of grinding it in a mortar and pestle, and even after cleaning it, I could smell it weeks later
Cool!
hexagons are the bestagons
can you do some energetics chemistry in the future? i like that type of stuff.
Luminol is good alternative for diphenyloxalates.
Ah, yes, the branch of the craziest element on the periodic table and how it bonds to itself or hydrogen. It's a literal sandbox, anything, no matter how crazy it sounds (should be) is possible
Edit: I'm gonna get ahead of the comments about tar and say, if you do, I'll report you without thinking twice
make glowing glass with this if possible
7:19 unexpeccted kujawski olej appeared
Why did you need to wait for it to cool? Couldn't you have filtered it when the desired crystals appeared while hot? That way they don't have the potential to be over-brominated while the reaction continues. Then you could just repeat the process with the filtrate until you're happy with the yield.
Mmhhmm glowstics.... Tasty!
Sounds like you have an inverse solubility problem with trying to get your crystals. Hot filtering might work. Edit: no idea why it didn't recrystalize when heated for distillation.
Now replace the oxonium with a suphonium.
How does it perform as a part of a dye sensitized solar cell? What about some of the side products?
How do I make acetonitrile?
Is it water soluble? Does it change colour based on the pH?
Algorithm changed. Video didn’t appear in my feed at all, all I get anymore on home page is new channels/discovery
Biblically accurate carbon molecule
I'm missing the drawn mechanism of the first condensation
Like marzipan right?
How difficult is to come up with a random molecule and try to synthesize it yourself by creating your own synthesis plan
Pretty much impossible, but it depends on the target compound
@@RiehlScience how then chemists come up with synthesis plan for new compounds
Maybe you left the reaction running for too long and so you didn't get those orange crystals.
O KURWA CZY TO GLOWING CANCER JUICE
jakiej kamery używasz?
Have you heard of Telomir 1 ❤ live forever lol 🎉😂❤
👌👌👌
Hi, please make eadible things like nilered in some video
You can actually eat any chemical, some of them you can even eat twice
Mmmmm, deep fried 2-naphthol ☺️☺️☺️
this guy makes videos every 5 days or sumthin like that unlike nilered, and his videos are more interesting, but the voice is killing me
First!
Benzenoic waste disposal? How does all that dye solution get dealt with
Yo fifth comment
The Girl Scouts called they say come pick up your brownie badge
Wow, you're uploading so many new videos as Trump is lying in one hour. 👍👍👍
I have a question @amuatur chemistry