Spiro[1H-azulenium-1,9′-fluorene] perchlorate. Intramolecular charge-transfer interaction between orthogonally arranged units of the azulenium cation and fluorene |
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| Authors: | Mitsunori Oda Nobue Nakajima Shigeyasu Kuroda |
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| Institution: | a Department of Chemistry, Faculty of Science, Shinshu University, Asahi 3-1-1, Matsumoto, Nagano 390-8621, Japan
b Department of Applied Chemistry, Faculty of Engineering, University of Toyama, Gofuku 3190, Toyama 930-8555, Japan |
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| Abstract: | Spiro1H-azulenium-1,9′-fluorene] (3) perchlorate was synthesized in five steps starting from fluorenone and trimethylsilyl enol ether of 1-acetylcycloheptatriene. The pKR+ value of 3 was determined to be 7.8. A characteristic absorption band of 3 in acetonitrile was observed at 430 nm, which shows a bathochromic shift in dichloromethane, indicating the first example of the intramolecular charge-transfer interaction between orthogonally arranged units of an azulenium ion having a tropylium ion ring and fluorene having two benzene rings. |
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