Saturday, January 11, 2020

organic chemistry - Can a molecule contain a linear series of conjugated pi bonds twisted through 180 degrees?


Imagine a long chain of carbon atoms connected by single and double bonds in conjugated fashion. All of the p orbital pi bonds would normally be aligned to either side of the carbon atoms forcing the molecule to adopt a flat structure. Would it be possible to take this structure and twist it slightly so as to form a long helical shape?


The bond overlap would not be as good but if the chain were long enough I would have thought the bond weakening would not be excessive. Obviously both ends would need to be firmly bonded to some other inflexible linking components such as a large protein molecule or a long chain of aromatic rings.


Has anything like this ever been synthesised? Is it even possible?



Here is an exampleconjugate chain either end of this structure would be connected to a larger molecular segment that would hold it in place and prevent it from untwisting. I want to give this normaly flat structure a 180 degree twist.




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