13 In one of the more spectacular examples of recent photochromic research, Jiro Abe and Co., in a very recent Organic Letters ASAP (doi: 10.1021/ol801135g), have demonstrated the very rapid formation and disappearance of a “green shit colored chromophore” upon shining UV light into a tube filled with a hexaarylbiimidazole derivative (vide infra, bitch).
The reaction is rapid and, most interestingly, rapidly reversible, which means that the formation of the green colored product is short lived and the color disappears, most notably faster than the diffusion forces can dissipate the greenish cloud. While the technology isn’t quite new, I’d have to say this is actually published in the incorrect journal. This is potential JACS and/or Angew material, given the rate of reversal and the demonstrable theatrics. Org Lett is an interesting journal and I don’t wince at publishing there, but “greener” pastures should have been waiting for this little idea. For example, if you own a pair of transition lenses, perhaps “green shit color” isn’t quite the tint you’re going for, but you’d be happy to know that formation of that tinge would be instantaneous upon exposure to UV light and its disappearances just as instantaneous. That beats unwittingly walking into a stairwell without realizing it because your goddamn glasses are still tinted from being outside.
To be sure you are as amazed as me, here is a YouToube from a movie in the SI:
“Posted with permission from Org. Lett., ASAP Article, 10.1021/ol801135g, Web Release Date: June 19, 2008.
Copyright © 2008 American Chemical Society.”
Obviously pretty fucking wicked. The visual splendor may not be sufficient, but the paper goes to great lengths to explain and characterize this process and does so in excellent fashion.
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Neat video. So, this isn’t really my field, but is this the kind of reaction that you can predict would happen, or is this more the kind of thing you just stumble upon?
Btw, the DOI you have is right, but your link for it is broken.
The paper lead me to believe that the idea was arrived at a priori and, really, the novelty wasn’t so much in the structure but the rate of formation and reversal of the color which, I assume, was something of a surprise. I emailed the prof, but he disregarded me (as they almost always do).
whoa, i really like that video. cool videos = real science.
Does derivation on video count?
So, I agree this could have done better than Org. Lett., but after reading through this a little more carefully, I see why they did.
There are still some unanswered questions they need to work out. For instance, why it worked in their NDPI system so much better than it did in their TPID system.
Also, I now see why they were flickering around the UV light so fast; not only to show how fast it works, but because the rapid photobleaching that takes place under continuous irradiation. That’s a problem that they’d need to work out, if it were going to be applied, say in the sunglass example you discussed.
Seems like a good idea just to get their idea out there somewhere, then when they go ahead and work that stuff out they can put it somewhere bigger.
I think the rapid photobleaching is one of the best things. Either you’re confused or I’m confused, but they make nothing out of the photostability of the compounds, or how quickly they degrade into inert side products. The rapid photobleaching is why it would make an excellent material for transition lenses and the like.
Photobleaching ruins the compound permanently, not just reverting it to clear, but making it incapable of greening again.
I almost posted that! Glad someone did. It’s cool.
E pluribus unum. Triplet states aid international Islamo-fascism! Sigma-rho correlations, fuse some rings, add a transition metal in a resolved chiral environment… Why are grad students allowed to go home – or even wash – until the work is done? Chain them to their benches, epoxy on Texas catheters, have at it. Add a microsecond synchrotron radiation crystal structure at the end.
If it doesn’t have a photoisomerizable Ar-N=N-Ar or a rotaxane, how good can it be? And why not more nitrogens from Click chemistry? Reduce organic chemistry’s carbon footprint!
Sure! This could have been published in JACS or A.C.. Considering the kind of anecdotes they publish at the moment this fits more than well in those journals. Moreover, it contains no equations so its perfect for the kind of reader their editors are working for.
Uh-oh. You sound like a man scorned. Damn that JACS! Damn it to hell!
What would the internet be without scornful anonymous haters of anything? It’s literally been hours, HOURS, since the last equation I saw in JACS and that really isn’t fucking good enough.
Zartan? I don’t know any “Zartan!”
Probably the coolest application of photochromics =)