Synthesis and structural study of 2-arylbenzotriazoles related to Tinuvins

A total number of nineteen 2-arylbenzotriazoles related to the UV absorber Tinuvin P have been studied. Moreover, besides those bearing a 2′-hydroxy substituent, known to experience ESIPT (Excited-State Intramolecular Proton Transfer), we have also prepared three compounds having another ortho-hydro...

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Bibliographic Details
Published inTetrahedron Vol. 69; no. 14; pp. 3027 - 3038
Main Authors Santa María, Dolores, Claramunt, Rosa M., Bobosik, Vladimir, Torralba, M. Carmen, Torres, M. Rosario, Alkorta, Ibon, Elguero, José
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 08.04.2013
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ULTRAVIOLET STABILIZERS
ABSORBER
FLUORESCENCE
DATABASE
MOLECULAR-ORBITAL METHODS
PHOTOSTABILITY
STATE
PROTON
NITRO
DEACTIVATION
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Summary:A total number of nineteen 2-arylbenzotriazoles related to the UV absorber Tinuvin P have been studied. Moreover, besides those bearing a 2′-hydroxy substituent, known to experience ESIPT (Excited-State Intramolecular Proton Transfer), we have also prepared three compounds having another ortho-hydroxy group at position 6′. The X-ray molecular structures of five key representatives have been determined and some important features related to their behavior discussed on the basis of solution and solid-state NMR, as well as B3LYP/6-311++G(d,p) computational results. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.01.096