Development of Persistent Triplet Diarylcarbenes by using Halogen Groups

2014 Fiscal Year Final Research Report

• Project/Area Number: 24550047
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Mie University
• Principal Investigator: HIRAI KATSUYUKI 三重大学, 社会連携研究センター, 准教授 (80208793)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Keywords: 三重項カルベン / ジアゾ化合物 / ハロゲン基 / 立体保護

Outline of Final Research Achievements

Three diaryldiazomethanes having halogen groups, which are inert to a triplet carbene, as steric protectors were synthesized, and the corresponding triplet diarylcarbenes were generated by photolysis of them and were characterized. Diphenylcarbene having four iodine groups at the ortho positions is observed up to 200 K in 2MTHF and has 18.4 minutes of half-life in degassed benzene at room temperature. Diphenylcarbene having two iodine groups and a trifluoromethyl group at the ortho positions is observed up to 100 K in 2MHF and has 40 ms of half-life in the benzene solution. (Triazol-5-yl)(phenyl)carbene having two 2,6-difluorophenyl groups at the 1,4-positions of the triazole ring is stable to 220 K in 2MTHF and is estimated to be a persistent triplet carbene as same as the tetraiodo-diphenylcarbene.

Free Research Field

物理有機化学