synthesis of fluorescent dyes

[Comandante]

does anyone have any knowledge about the synthesis of any of the following dyes, or any other fluorescent dyes for that matter that I could possibly make without too much effort and resources, provided of course, i dont get any poisonous gases ;

 

9,10-diphenylanthracene

 

9,10-bis(phenylethynyl)anthracene

 

5,6,11,12-tetraphenylnaphthacene

 

I was previously extracting dyes from the lightsticks but they're damn expensive! (around $1.20 per 20mL the cheapest i got)

[YT2095]

you should add 1,Chloro,9,10,Diphenylanthracene to that list also

it`s on my shopping list too!

 

Eosin from Fluorescein is my latest project, erythosin is another I`ve made but Eosin is by far more striking as a color.

 

you Will need to start with Fluorescein though.

 

have you got a source for Phenyl Oxalate, I`m after that also

[Comandante]

ah, apart from the basic stuff I synthesized at first year uni I haven't done any other so I suppose I'd have to start with some basic dyes... I used hydrogen peroxide from the shops tho with dyes from the commercial light sticks (my fav 9,10-bis(phenylethynyl)anthracene - at least i think that's the one - for green) and I figured they put something else in the peroxide in the lightsticks, apart from the catalyst, there's something else still as the same conc of peroxide I made doesn't work the same as same conc of peroxide from the lightsticks... anyway, using peroxide from lightsticks and 2 different dyes I did a nice little light-up today in what ended up as greenish glow; see attachment

 

I wish I knew how to make this dye... doesn't seem to float around the net that freely

[Comandante]

as for phenyl oxalate I think I might know where to get it from cheap I'll get back to you if I find it but don't think you'll have local retailer anyway.. but I think that's easy to make isn't it? just need ..the ingredients

[YT2095]

Wow, beautiful pic/demo!

 

what did you use for that one?

 

as far as I can tell, phenyl oxalate + (dyes listed above) + H2O2 should work.

and yeah, I can make the ester easily enough, I just need to get hold of the Phenol

[Comandante]

Wow, beautiful pic/demo!

 

what did you use for that one?

 

as far as I can tell, phenyl oxalate + (dyes listed above) + H2O2 should work.

and yeah, I can make the ester easily enough, I just need to get hold of the Phenol

 

Thanks

First mixed 2 different dyes (9,10-diphenylanthracene and 9,10-bis(phenylethynyl)anthracene in about 50:50 ratio (a total of 25mL), then added about the same volume (25mL) of H2O2 into a 50mL flask. I also think that in H2O2 there was salicylic acid as a catalyst. Also, just to comment, I don't think phenyl oxalate was used in mixture with dyes as wiki suggests, because these light sticks were made to work over 8hrs and for that I think they've used bis(2,4,5-trichlorophenyl-6-carbopentoxyphenyl)oxalate (CPPO) (again, as wiki suggests).

 

HOWEVER, I noticed that these two dyes mixed together gave significantly brighter glow at approximately steady intensity for only about half an hour (might not look that bright in the photo but I assure you it lit the entire room so you could read a book under its light, it's just that camera exposure caused the blackness around, the intensity was about the same as that of 2 candles I would say) and for further half an hour showed steady decrease until it eventually was so dim you couldn't see it glow with 60W light bulb turned on in the room, but was nevertheless visible in the dark for another few hours.

 

Also, since these two dyes gave off photons from the same side of the spectrum I'd assume that halped increase the overall intensity but not sure with that. Next I'll try using dyes for blue and yellow in a mix to see if I'll get green light and if the intensity will be the same as with blue and green and how long it will last.

 

By the way, is there a way to test for salicylic acid in the peroxide?

 

ah, one more thing,

You can make phenol from cumene - http://en.wikipedia.org/wiki/Cumene

if you click on the Cumene process it tells you how (not something I'd attempt yet but perhaps you can give it a go if you have the resources http://en.wikipedia.org/wiki/Cumene_process

 

You can also make phenol by reacting benzenesulfonic acid with sodium hydroxide, as well as with hydrolisis of chlorobenzene.

[Externet]

Hi.

Not on fluorescent, but a pretty site to mark and enjoy:

 

http://www.jcsparks.com/painted/pigment-chem.html#Brazil

 

Miguel

[Comandante]

nice site Miguel

 

YT2095; Don't know if you know of this supplier but I came accross it just yesterday and it seems like they've got retailers in lots of countries, sounds familiar though but I've never heard of it, and they've got everything; http://www.sigmaaldrich.com Check it out if you haven't.

[YT2095]

I have heard of them, and they ask way too many questions also, the Home chemist or the likes will be highly unlikely to get anything from them.

I have a different supplier here in the UK, they also ask plenty questions, but are amenable to the private individual if you`re not a dickhead

and the order minimum is £50.

[Comandante]

ah, so it's not worth even trying to order then is it i need to find myself a nice supplier here in aus... hard task, easier to just make the stuff if you possibly can.

[woelen]

Official chemical suppliers like Aldrich, Alfa-Aesar, etc. do not sell to individuals. They only sell to companies with registered lab-facilities and to universities, schools, etc.

[John Cuthber]

They don't seem to be easy to find out about.

This

http://www.springerlink.com/content/w60054l7wu642728/

gives some data on the first dye

and the last experiment here

http://www.mtholyoke.edu/courses/menunez/Chm302OrgIIWeb/Labs1-6.pdf

might be interesting too.

[YT2095]

I like this site too: http://www.chem.leeds.ac.uk/delights/texts/VV_exp_26_files/VV_exp_26c.htm

[Comandante]

They don't seem to be easy to find out about.

This

http://www.springerlink.com/content/w60054l7wu642728/

gives some data on the first dye

and the last experiment here

http://www.mtholyoke.edu/courses/menunez/Chm302OrgIIWeb/Labs1-6.pdf

might be interesting too.

 

Nice find on springerlink. Chinese work hard on chem eng. And citing the full article here "Bis(2-butoxycarbonyl-3,4,6-trichlorophenyl) oxalate was prepared

in advance with an established procedure [2]; alternatively, it is also

available from Fluka." you can see that the document shows only half the story, nevertheless I found the "Procedure" section most interesting to read as it tells how everything is done. I concluded however that I don't have sufficient resources to repeat the procedure, so I might just leave it on that for now, unless someone else comes up with another way

 

YT2095; Been there on that site of yours, not bad at all.

 

By the way I tried the yellow+blue dye but the color remained yellowish and with much smaller glow intensity, although it may look bright on this video the green one was much brighter; http://www.youtube.com/watch?v=N-RYZz7UQ8s

 

Did you find that patent yet ?

[gary ellis]

You may want to check out US patent 6,126,871 from Omniglow corporation. They claim that the addition of esters like triethyl citrate greatly enhance the intensit of the light emission.

 

I am also looking for a prep method for 9,10-diphenylanthracene.

[alan2here]

Nice picture on the third post Sysco.

[Comandante]

You may want to check out US patent 6,126,871 from Omniglow corporation. They claim that the addition of esters like triethyl citrate greatly enhance the intensit of the light emission.

 

I am also looking for a prep method for 9,10-diphenylanthracene.

 

Nice find. Some useful info there.

 

Nice picture on the third post Sysco.

 

Thanks I need a new camera though

[YT2095]

*Bump*

 

Sysco, I`ve just had an order in from a fella at: http://www.scuddlebutt3.co.uk/

I ordered the Deluxe fluorescent dye kit, it Might be worth a look, I know the quantities don`t sound a lot, but trust me, there`s Plenty!

the Rhodamine B is fantastic as is the Optical Brightener.

 

take a peek anyway

[Comandante]

Hey, that sure is a nice deal! I might consider it, though I've recently been in contact with a reseller from China who has some nice deals too, but he ships dyes in solution (as those in light sticks) already so I'd have to work out whether concentration is worth it as compared to that site of yours.

 

But since they accepts paypal too, I'll definitely look into it, and also because they say "The dyes in this kit are some of the most intense dyes known, many visible at parts per million concentration." and so as little as 5grams would be quite plenty as you say!

 

Thanks!