Molbank 2005, M412 |
Chemistry
Department, Faculty of Science,
Jeddah
21413,
Tel.
(+966)-2-6952293, Fax (+966)-2-6952293, e-mail: [email protected]
Received:
Keywords: cyclopentanone, aldol
condensation, ferrocen
There is considerable interest in the synthesis of new
materials with large second-order optical non-linearity because of their
potential applications in optical data storage, telecommunications and optical
signals processing [1-4]. First and second hyperpolarizability
can be observed with molecules which possess an electron donor and acceptor
groups connected by a conjugated ¦°-electron bridge which allow the possibility
of intramolecular charge transfer [5-6].
To
a well stirred solution of (Fc-CHO) (2.5g, 11.7 mmole) cyclopentanone (0.98 g,
15.8 mmole) in ethanol (30 mL)
was added dropwise a solution of NaOH
(30 mL, 10%) at 60¡ãC over a period of 20 minutes.
After the addition was completed the solution was left to stir at room
temperature for 12 hours, and then poured into ice-cold water (200 ml) and stir
for 2 hours. The precipitated chaconne was filtered off and washed with copious
amount of water until the wash was neutral, then washed with cold ethanol and
dried. The solid products were recrystallized from
ethanol to give yellow crystals (5.2 g, 93.4%).
Melting
Point: 200-202 ¡ãC
(uncorrected).
UV
(EtOH, ¦Ëmax
nm; ¦Å dm3.mol-1.cm-1): 350 (46692); 525
(12356).
IR (KBr; cm-1): 1690 (C=O); 1625, 1610 (C=C); 1110, 990, 813.
1H-NMR (400 MHz; CDCl3):
¦Ä= 7.44 (s, 2H, -CH=C); 4.60 (broad s, 4H, H-2, H-5); 4.51 (broad s, 4H, H-3, H-4);
4.17 (s, 10H, C5H5); 2.81 (broad s, 4H, CH2).
Elemental
Analysis: Calculated for C27H24OFe2 (476.27):
C, 68.13%; H, 5.04%. Found: 68.25%; H, 4.91%.
References:
1. Boyd, R. W. Nonlinear
Optics, Academic Press,
2. Marder, S. R., Beratan, D. N., Cheng, L. T. Science, 1991, 252(103).
3. Eaton, D. F. Science, 1991, 253(281).
4. Staring, E. G. Recl. Trav.
Chim. Pays-Bas, 1991, 110(492).
5. Derik, C.W., Wagniere,
R. J. J. Am. Chem. Soc. 1986, 5387 (108).
Sample Availability: Available from MDPI.
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