Azulene - an interesting blue organic compound

  • Thread starter Thread starter Astronuc
  • Start date Start date
Click For Summary
Azulene is a bicyclic organic compound found in certain blue mushrooms and sea creatures, notable for its unique structure resulting from the fusion of cyclopentadiene and cycloheptatriene rings. It features a 10 pi electron system, distinguishing it from compounds like indole. Recent discussions highlight azulene's ability to defy Kasha’s Rule due to its excited-state (anti)aromaticity, which may have implications for solar power technology. Its blue color is unexpected for a conjugated system of this size, challenging conventional assumptions in chemistry. Azulene's intriguing properties have garnered attention in scientific research, indicating its potential for future applications.
Astronuc
Staff Emeritus
Science Advisor
Gold Member
Messages
22,416
Reaction score
7,281
I was reading an article about some interesting features of azulene, a bicyclic organic compound that is apparently present in some blue mushrooms and sea creatures. So, I decided to learn more out of curiosity.

Azulene is usually viewed as resulting from fusion of cyclopentadiene and cycloheptatriene rings. Like naphthalene and cyclodecapentaene, it is a 10 pi electron system.
https://en.wikipedia.org/wiki/Azulene

It is different than indole - https://en.wikipedia.org/wiki/Indole

Excited-State (Anti)Aromaticity Explains Why Azulene Disobeys Kasha’s Rule​

https://pubs.acs.org/doi/10.1021/jacs.3c07625

Knowledge of how the renegade azulene can flout the rules may help scientists harness its energy for solar power tech, according to Popular Mechanics.
. I'm not going to link to the article, since the comment seems overly speculative for now. Suffice it to say that azulene has attracted some attention in the chemistry research area.
 
Chemistry news on Phys.org
Surprising that this is blue. Usually conjugated systems of this size would be yellow/orange. Just goes to show that intuition sometimes leads to spurious conclusions.
 
What I know and please correct me: a macroscopic probe of raw sugar you can buy from the store can be modeled to be an almost perfect cube of a size of 0.7 up to 1 mm. Let's assume it was really pure, nothing else but a conglomerate of H12C22O11 molecules stacked one over another in layers with van de Waals (?) "forces" keeping them together in a macroscopic state at a temperature of let's say 20 degrees Celsius. Then I use 100 such tiny pieces to throw them in 20 deg water. I stir the...

Similar threads

  • · Replies 3 ·
Replies
3
Views
4K
  • · Replies 6 ·
Replies
6
Views
4K
  • · Replies 3 ·
Replies
3
Views
2K
  • · Replies 8 ·
Replies
8
Views
4K
  • · Replies 4 ·
Replies
4
Views
10K