Polycyclic fused ring type π-conjugated organic...

Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing

Reexamination Certificate

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C556S431000, C556S432000

Reexamination Certificate

active

07973190

ABSTRACT:
A polycyclic fused ring type π-conjugated organic material (VIIa, VIIb, VIIc, VIId) is obtained in the following manner. That is, as shown in Scheme 1 below, a starting material (I) is dimetalated with an organometallic base. The starting material (I) thus dimetalated is trapped with an organosilicon reagent (i: (1) n-BuLi or t-BuLi; (2) HMe2SiCl). As a result, an intermediate is obtained. Thereafter, the intermediate is allowed to react with a metal reductant. This causes an intramolecular reductive cyclization reaction to proceed. As a result, a dianion intermediate is produced. The dianion intermediate is trapped with an electrophile (ii: (1) LiNaph, THF, rt, 5 min; (2) electrophile or NH4Cl) In this way, the polycyclic fused ring type π-conjugated organic material is obtained. The polycyclic fused ring type π-conjugated organic material, an intermediate therefor, a method for producing the polycyclic fused ring type π-conjugated organic material, and a method for producing the intermediate make it possible to provide a polycyclic fused ring type π-conjugated organic material having excellent light-emitting and charge-transporting properties.

REFERENCES:
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patent: 2006/0100433 (2009-11-01), None
patent: 2004/018488 (2003-08-01), None
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Yamaguchi, Shigehiro et al. Bis-Silicon-Bridged Stilbene Homologues Synthesized by New Intramolecular Reductive Double Cyclization, Journal of the American Chemical Society, 2003, vol. 125 No. 45, p. 13662-13663.
M. Serby, S. Ijadi-Maghsoodi, and T.J. Barton. “Synthesis and Chemistry of a Trisiladibenzo-Cyclodiyne”. XXXIIIrd Symposium on Organosilicon Chemistry, Abstract No. PA-35, Apr. 6-8, 2000, Saginaw, Michigan, USA.
European Office Action dated Jul. 21, 2009.

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