Photo and Collision Induced Isomerization of a Cyclic Retinal Derivative: An Ion Mobility Study.
A cationic degradation product, formed in solution from retinal Schiff base (RSB), is examined in the gas phase using ion mobility spectrometry, photoisomerization action spectroscopy, and collision induced dissociation (CID). The degradation product is found to be N-n-butyl-2-(β-ionylidene)-4-methylpyridinium (BIP) produced through 6π electrocyclization of RSB followed by protonation and loss of dihydrogen. Ion mobility measurements show that BIP exists as trans and cis isomers that can be interconverted through buffer gas collisions and by exposure to light, with a maximum response at λ = 420 nm.Graphical Abstract.
School of Chemistry, University of Melbourne, Melbourne, Australia.
Neville J A
NJ
Coughlan
School of Chemistry, University of Melbourne, Melbourne, Australia.
Michael S
MS
Scholz
School of Chemistry, University of Wollongong, Wollongong, Australia.
Christopher S
CS
Hansen
School of Chemistry, University of Wollongong, Wollongong, Australia.
Adam J
AJ
Trevitt
School of Chemistry, University of Melbourne, Melbourne, Australia.
Brian D
BD
Adamson
School of Chemistry, University of Melbourne, Melbourne, Australia. evanjb@unimelb.edu.au.
Evan J
EJ
Bieske
Collision induced isomerization; Ion mobility; Ion spectroscopy; Photoisomerization; Retinal