Über polyarylenalkenylene und polyheteroarylenalkenylene, 13. Synthesen und charakterisierung von poly (dithieno[3,2‐b: 2′, 2′,3′‐d]thiophen‐2, 6‐diylvinylenarylenvinylen)en und einigen modellverbindungen

Abstract

Synthesen und Charakterisierung von Poly(dithieno[3,2-b : 2 ',3 '-dl thiophen-2,6-diylvinylenarylenvinylen)en und einigen Modellverbindungen SUMMARY:From Wittig-reactions of dithieno[3,2-b: 2',3 '-d]thiophene-2,6-dicarboxaldehyde (1) with "mono-and bis-Wittig-salts" of the benzene and thiophene series poly(dithieno[3,2-b: 2',3'-d]thiophene-2,6-diylvinylenearylenevinylene)s 3 ac and some model compounds 5 ac were obtained. Wittig-reactions of dithieno[3,2-b: 2',3'-d]thiophene-2-carboxaldehyde (6) with "mono-and bis-Wittig-salts" gave model compounds 7a-c and 8a, c. The structures of all compounds were confirmed by elemental analyses, 1Rand electronic spectra, those of the model compounds additionally by mass spectra, and in case of sufficient solubility by 'H NMR spectra. The electrical conductivities of all compounds and the thermooxidative degradation of the polymers 3a, c were investigated. EinleitungDie vorliegende Reihe beschreibt die Synthesen einer gronen Zahl polymerer Vinylene rnit verschiedenen, insbesondere heterocyclischen Baueinheiten sowie die Einfliisse ihrer chemischen Struktur auf die elektrischen Eigenschaften. Die rnit der vorangegangenen Arbeit iiber Poly(thieno[2,3-b] thiophen-2,5-diylvinylenarylenvinylen)e und Poly(thieno(3,2-b]thiophen-2,5-diylvinylenarylenvinylen)e I ) begonnenen Untersuchungen iiber den Einbau kondensierter Thiophensysteme in polymere Vinylene sollen hier rnit dem Dithieno[3,2-b: 2',3'-dlthiophen weitergefiihrt werden. Synthese der polymeren VinyleneWittig-Reaktion von Dithieno[3,2-b: 2',3 '-d]thiophen-2,6-dicarbaldehyd (1) rnit 4-(Triphenylphosphoniomethyl)benzyltriphenylphosphoniumdibromid (2a) unter Stickstoff in absolutem DMF rnit Kalium-tert-butoxid als Base ergab in 68proz. Ausbeute das schwarzrote Poly(dithieno[3,2-b: 2',3'-d]thiophen-2,6-diylvinylen-1,4phenylenvinylen) (3 a). Analog wurde aus 1 und 2,5-Dimethoxy-4-(triphenylphosphoa) 12. Mitteilung: cf. I).

Vibrational and Quantum‐Chemical Study of Nonlinear Optical Chromophores Containing Dithienothiophene as the Electron Relay

“…The dried product was treated with n ‐hexane, in which the unreacted starting material is completely soluble but not the product. The final yield of the DTT–A 1 product (spectroscopic data were in accord with those previously described)34 was 0.85 g (83 %). 1 H NMR (CDCl 3 ): δ = 7.29 (d, 1 H, J = 4.3 Hz), 7.57 (d, 1 H, J = 4.3 Hz), 7.97 (s, 1 H), 9.96 ppm (s, 1 H); EI‐MS: m / z (%): 224 ([ M + ], 52), 195 (19), 151 (47), 93 (52), 69 (100).…”

Poly(thieno[3,4-b]thiophene). A New Stable Low Band Gap Conducting Polymer

“…Several examples of conducting polymers derived from thieno[2,3-b]thiophene 11 and thieno[3,2-b]thiophene [12][13][14][15][16][17] have been reported. The chemical structures of these monomers are depicted in Figure 1.…”