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Cocrystals derived from 1,1?-bis(ethenyl-4-pyridyl)ferrocene (1) and resorcinol/phloroglucinol and a crystal of 1,1?-bis-(ethenyl-4-quinolinyl)ferrocene (5) have been studied with the aim of engineering crystalline NLO materials. X-ray structure analyses revealed a NLO active syn-type molecular conformation of 1 and 5 via hydrogen bonding with resorcinol/phloroglucinol and pi-pi interaction between quinoline rings, respectively. For 5, all molecular dipoles are aligned in the same direction and the SHG efficiency is about 4 times that of urea. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
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Reference：
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion