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1,3-Dibromoisothianaphthene would be an alternative building block for conjugated polymers through Pd[0]-catalyzed coupling reactions. We attempted to make this compound through bromination of isothianaphthene using N-bromosuccinimide. That process led to only intractable black solid presumably due to oxidative polymerization. We did not pursue further in this direction for the following reasons: (i) The only example of this compound was described in a patent as a reaction intermediate (Itoh, K. U.S. Pat. Appl. Publ. US 2006057426, 2006, 8 pp, The compound was not isolated or characterized. The stability of this compound is also questionable since the similar compound, 1,3-dichloroisothianaphthene. which is expected to be more stable, decomposes with time even at low temperature under an inert atmosphere (ref 27, ii) It is generally accepted that in a Pd[0]-catalyzed coupling reaction the rate-limiting step is the oxidative insertion of aryl halide to the Pd species. The elec
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1,3-Dibromoisothianaphthene would be an alternative building block for conjugated polymers through Pd[0]-catalyzed coupling reactions. We attempted to make this compound through bromination of isothianaphthene using N-bromosuccinimide. That process led to only intractable black solid presumably due to oxidative polymerization. We did not pursue further in this direction for the following reasons: (i) The only example of this compound was described in a patent as a reaction intermediate (Itoh, K. U.S. Pat. Appl. Publ. US 2006057426, 2006, 8 pp). The compound was not isolated or characterized. The stability of this compound is also questionable since the similar compound, 1,3-dichloroisothianaphthene. which is expected to be more stable, decomposes with time even at low temperature under an inert atmosphere (ref 27). (ii) It is generally accepted that in a Pd[0]-catalyzed coupling reaction the rate-limiting step is the oxidative insertion of aryl halide to the Pd species. The electron-rich isothianaphthene may thus slow down the insertion and destabilize the complex leading to side reactions and possible deactivation of the catalyst; see for example: Espinet, P.; Echavairen, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704-4734.
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Wudl et al. reported the preparation of a 1,3-dimercuryisothianaphthene derivative in 1978; see:Wudl, F.; Kruger, A. A.; Thomas, G. A. Ann. N.Y. Acad. Sci. 1978, 313, 79-85. 1,3-Dilithioisothianaphthene is another example of dimetallic ITN derivative that has not been isolated and thus could only be used as reaction intermediate.
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8 (∼15 mg/mL) and did not precipitate after the solution was cooled back down to room temperature.
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8 (∼15 mg/mL) and did not precipitate after the solution was cooled back down to room temperature.
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2/(V s) was observed, presumably due to its amorphous nature.
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2/(V s) was observed, presumably due to its amorphous nature.
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We are currently optimizing the reaction conditions and searching for other possible types of monomers and coupling reactions toward polymers with better properties, especially higher molecular weights. For example, a sample of PITN-co-Fl of higher molecular weight (Mn, 7700, M w, 13 100, PDI, 1.7) was obtained using Pd[P'Bu 3]2 (2 mol , as the catalyst in THF at 80 °C for 24 h. We have also synthesized a 1,3-diborylated ITN derivative (B2ITN) that shows much enhanced stability toward air and moisture; see Supporting Information for synthetic conditions and NMR characterization. We are currently investigating its polymerization with different dihalides through Suzuki-type coupling reactions
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2ITN) that shows much enhanced stability toward air and moisture; see Supporting Information for synthetic conditions and NMR characterization. We are currently investigating its polymerization with different dihalides through Suzuki-type coupling reactions.
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