Organometallic−Organic Hybrid Crystals from Ferrocenyl Dipyridine and Binaphthol:  Different Crystal Structures and Nonlinear Optical Properties Depending upon the Reaction Medium and Optical Purity of Binaphthol

The hydrogen bond directed molecular recognition between 1,1‘-bis(ethenyl-4-pyridyl)ferrocene (1) and (±)-1,1‘-binaphthol (2)/(−)-1,1‘- binaphthol ((−)-2) has been studied by cocrystallization in different solvents. Single-crystal X-ray structures reveal that 3:2, 2:1, and 1:1 complexes (3, 4, and 5...

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Bibliographic Details
Published in:Organometallics 1999-11, Vol.18 (24), p.5080-5085
Main Authors: Lee, In Su, Chung, Young Keun, Mun, Junho, Yoon, Choon Sup
Format: Article
Language:English
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Summary:The hydrogen bond directed molecular recognition between 1,1‘-bis(ethenyl-4-pyridyl)ferrocene (1) and (±)-1,1‘-binaphthol (2)/(−)-1,1‘- binaphthol ((−)-2) has been studied by cocrystallization in different solvents. Single-crystal X-ray structures reveal that 3:2, 2:1, and 1:1 complexes (3, 4, and 5, respectively) of 1,1‘-bis(ethenyl-4-pyridyl)ferrocene (1) and (±)-1,1-binaphthol (2) are formed in tetrahydrofuran, methanol, and ethanol, respectively. 5 has a noncentrosymmetric packing arrangement, and an efficiency of 0.3 times that of urea in second-harmonic generation has been measured at 1295 nm. An X-ray crystal structure of 6, 1:1 complex of 1 with (−)-2 in ethanol, reveals that all the molecular dipoles are aligned in the same direction (i.e, a polar crystal), but 6 has modest nonlinear optical properties (ca. 0.4 times that of urea).
ISSN:0276-7333
1520-6041
DOI:10.1021/om990544d