31590-12-2Relevant academic research and scientific papers
Highly Substituted Δ3-1,2,3-Triazolines: Solid-State Emitters with Electrofluorochromic Behavior
Suleymanov, Abdusalom A.,Ruggi, Albert,Planes, Ophélie Marie,Chauvin, Anne-Sophie,Scopelliti, Rosario,Fadaei Tirani, Farzaneh,Sienkiewicz, Andrzej,Fabrizio, Alberto,Corminboeuf, Clémence,Severin, Kay
, p. 6718 - 6721 (2019)
Highly substituted Δ3-1,2,3-triazolines can be prepared by reaction of triarylvinyl Grignard reagents with functionalized organic azides. The heterocycles are fluorescent in the solid state, and—depending on the substituents—they can display aggregation-induced emission. Upon oxidation, the triazolines form stable radical cations with altered photophysical properties. Therefore, they represent rare examples of solid-state emitters with intrinsic electrofluorochromic behavior.
Photochemical generation of iminoquinone methides by 1,4-hydrogen migration in derivatives of o-tolylnitrene
Bucher, Goetz
, p. 2447 - 2462 (2007/10/03)
The photochemistry of a series of derivatives of o-tolyl azide, bearing a variety of substituents in the benzylic positions, has been investigated using matrix isolation spectroscopy and density functional calculations. It has been found that introduction of any substituent possessing a lone pair (i.e., R = Br, Cl, MeO, Me2N) allows a 1,4-hydrogen shift to take place, yielding iminoquinone methides. Additional methyl groups in the benzylic position, however, do not promote a photochemical conversion into iminoquinone methides. If the benzylic substituent itself is part of a ring system, the size of this ring plays an important role. Thus, 2-methyl-8-nitrenote-trahydroisoquinoline rearranges very easily, whereas 4-nitrenophthalan does not give the reaction. Density functional calculations [B3LYP/6-31G(d)] have been used to gain an understanding of the reaction. It has been found that the activation energies depend strongly on the nature of the substituent, being lowest if R = NMe2. Incorporation of the benzylic substituent into a ring reduces the flexibility of the system and results in significantly raised barriers.
Cyclization of Phenyl Azides with Homoallylic or Allylic Ortho Substituents and the Consequences of Triazoline Fragmentation
Smith, Peter A. S.,Chou, Shang-shing Peter
, p. 3970 - 3977 (2007/10/02)
o-(Allyloxy)phenyl azide (1) and 14 derivatives substituted on the allyl group were thermolyzed at 110-120 deg C to form benzoxazines (16), dihydroazirinobenzoxazines (17), or 3-alkenylbenzomorpholines (18, 19) through fragmentation of intermediate triazolines.With substituted allyl groups, the geometrical isomers gave the same products in the same ratio, except in the case of o-(β,γ-dimethylallyl)phenyl azide.Rearrangement by phenyl migrations occured with the β-phenylallyl compound. o-Allylphenyl azide (27a), (o-azidophenyl)acetaldehyde (27b), and o-phenyl azide (27c) required temperatures of 155-200 deg C for thermolysis and yielded 2-methylindole, oxindole, and 2-ethylbenzoxazole, respectively, by nitrene insertion.
