Synthesis and properties of naphthalene trimers linked by 1,3,4-oxadiazole spacers

Two types of naphthalene trimers linked by 1,3,4-oxadiazole spacers were synthesized and investigated for their physical and electronic properties. 2,6- and 2,7-isomers on central naphthalene moieties were obtained in the forms of pale yellow solids and colorless crystals, respectively. The melting...

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Bibliographic Details
Published in:Tetrahedron letters 2008-09, Vol.49 (40), p.5816-5819
Main Authors: Ono, Katsuhiko, Ito, Hiroki, Nakashima, Akihiro, Uemoto, Mariko, Tomura, Masaaki, Saito, Katsuhiro
Format: Article
Language:English
Subjects:
Molecular aggregation
Naphthalene
Oxadiazole
Regioisomer
π-Conjugation
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Summary:Two types of naphthalene trimers linked by 1,3,4-oxadiazole spacers were synthesized and investigated for their physical and electronic properties. 2,6- and 2,7-isomers on central naphthalene moieties were obtained in the forms of pale yellow solids and colorless crystals, respectively. The melting point of the 2,6-isomer was higher than that of the 2,7-isomer. An X-ray crystallographic analysis revealed a π-stacked column with a short intermolecular distance in the crystals of the 2,6-isomer. The absorption maximum of the 2,6-isomer was red-shifted as compared to that of the 2,7-isomer, indicating a π-conjugation between di-2-naphthyloxadiazole moieties in the 2,6-isomer. The quantum yields of the 2,6- and 2,7-isomers were measured to be 0.97 and 0.74, relative to that of 2,5-di-2-naphthyl-1,3,4-oxadiazole (0.85). Molecular orbital (MO) calculations demonstrated that the 2,6-isomer had a higher electron affinity than the 2,7-isomer. Thus, the crosslinking of building blocks is important for the design of functional materials.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.07.122