One-Pot Synthesis of Brightly Fluorescent Mes2B-Functionalized Indolizine Derivatives via Cycloaddition Reactions.
Four new BMes2-functionalized indolizine derivatives (Mes = mesityl) have been prepared via the cycloaddition reaction between pyrido[2,1-a]isoindole (A) or pyrrolo[1,2-a]pyridine (B) and BMes2-containing alkynes. All four compounds are brightly blue or blue-green fluorescent with λ(em) = 428-495 nm and Φ = 0.27-0.68, depending on the substitution position of the BMes2 group. Experimental and TD-DFT computational data indicated that the primary electronic transitions responsible for the fluorescence of 1-4 are from HOMO to LUMO (π → π*) rather than charge transfer from N → B, which is in agreement with previous findings suggesting that the lone-pair on N is delocalized throughout the N-heterocycles.
†Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada.
Deng-Tao
DT
Yang
‡Institut für Anorganische und Analytische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany.
Julian
J
Radtke
†Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada.
Soren K
SK
Mellerup
†Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada.
Kang
K
Yuan
†Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada.
Xiang
X
Wang
‡Institut für Anorganische und Analytische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany.
Matthias
M
Wagner
†Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada.
Suning
S
Wang