ChemInform Abstract: Facile Synthesis, Crystal Structure, and Solid‐State Fluorescence of Dicyclohexane‐Anellated Anthracene.

Abstract

Other polycyclic compounds Q 1150Facile Synthesis, Crystal Structure, and Solid-State Fluorescence of Dicyclohexane-Anellated Anthracene. -Diels-Alder reaction between in situ-generated 2,3-dehydronaphthalene and the dicyclohexane-fused furan (II) gives rise to adduct (IV). The transformation of (IV) into the dicyclohexane-anellated anthracene (V) is achieved by one-step deoxygenation with low-valent titanium. Intermediate (II) is obtained by homocoupling of cyclohexanone (I) with NiO2, followed by the Paal-Knorr furan synthesis. For comparison purposes the synthesis of dipropylanthracene (VIII) is presented. Compound (V) adopts anti-parallel face-to-face slipped π-stacking in its crystal structure, inducing an excimer-like emission, whereas the fluorescence of (VIII) is an exciton-like emission. -(KITAMURA*, C.; MATSUMOTO, C.; KAWATSUKI, N.; YONEDA, A.; ASADA, K.; KOBAYASHI, T.; NAITO, H.; Bull. Chem. Soc. Jpn. 81 (2008) 6, 754-756; Dep. Mater. Sci. Chem., Univ. Hyogo, Himeji, Hyogo 671, Japan; Eng.) -H. Hoennerscheid 39-088