The photoisomerization of cis,trans-1,2-dideuterio-1,4-diphenyl-1,3-butadiene in solution. No bicycle-pedal

Jack Saltiel; Christopher E Redwood; Ratheesh Kumar V K

doi:10.1039/c9pp00113a

The photoisomerization of cis,trans-1,2-dideuterio-1,4-diphenyl-1,3-butadiene in solution. No bicycle-pedal

Photochem Photobiol Sci. 2019 Sep 1;18(9):2174-2179. doi: 10.1039/c9pp00113a. Epub 2019 May 28.

Authors

Jack Saltiel¹, Christopher E Redwood¹, Ratheesh Kumar V K¹

Affiliation

¹ Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA. saltiel@chem.fsu.edu.

PMID: 31134259
DOI: 10.1039/c9pp00113a

Abstract

cis,trans-1,2-Dideuterio-1,4-diphenyl-1,3-butadiene (ct-DPB_d2) was synthesized and its cis-trans photoisomerization in cyclohexane-d₁₂ (C₆D₁₂) at room temperature was monitored by ¹H NMR spectroscopy. The results reveal formation of only trans,trans-1,2-dideuterio-1,4-diphenyl-1,3-butadiene (tt-DPB_d2). The failure to detect formation of trans,cis-1,2-dideuterio-1,4-diphenyl-1,3-butadiene (tc-DPB_d2) eliminates the possibility that an identity bicycle pedal process contributes to inefficiency in the cis-trans photoisomerization of cis,trans-1,4-diphenyl-1,3-butadiene (ct-DPB).