Thermal decomposition of o-azidobithienyls

Zanirato, Paolo; Spagnolo, Piero; Zanardi, Giuseppe

doi:10.1039/p19830002551

Cited by 52 publications

(30 citation statements)

References 6 publications

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“…It is worth noting that this one-step synthetic route of 3,3 0 -dibromo-2,2 0 -bithiophene is much more efficient than the reported synthetic routes, which require either multiple steps, or expensive chemicals, or both. [28,29] Subsequent amination of 1 with 2-hexyldecan-1-amine produced 3 (4-(2-hexyldecan)-4H-bisthieno [2,3-…”

Section: Resultsmentioning

confidence: 99%

Transistor Paint: Environmentally Stable N‐alkyldithienopyrrole and Bithiazole‐Based Copolymer Thin‐Film Transistors Show Reproducible High Mobilities without Annealing

Liu¹,

Zhang²,

Osaka³

et al. 2009

Adv Funct Materials

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New solution processable 4‐(2‐hexyldecan)‐4H‐bisthieno[2,3‐d:3′,2′‐b]pyrrole and 4,4′‐dialkyl‐2,2′‐bithiazole‐based copolymers (PBTzDTPs) are synthesized with excellent FET performance. These novel copolymers have considerable potential in printable electronics as they have high charge carrier mobilities, excellent air stability, good solution processibility, and no requirement for post‐deposition thermal annealing, all requirements for this field of application. The thin film transistors fabricated from PBTzDTPs achieve field effect mobilities as high as 0.14 cm2 V−1 s−1 with current on/off ratios up to 106 without thermal annealing. In addition, the devices exhibit stable performance in air, showing no significant degradation over 60 days. Moreover, the polymers described here provide an excellent example of the systems in which higher mobility performance does not require higher crystalline, long‐range ordered structures. Such a system appears to be particularly promising for rapid fabrication techniques, where kinetic conditions usually prevent the development of long‐range order.

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Section: Resultsmentioning

confidence: 99%

Transistor Paint: Environmentally Stable N‐alkyldithienopyrrole and Bithiazole‐Based Copolymer Thin‐Film Transistors Show Reproducible High Mobilities without Annealing

Liu¹,

Zhang²,

Osaka³

et al. 2009

Adv Funct Materials

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show abstract

“…Dithieno[3,2-b: [8] 2,7-dibromo-9,9-dihexyl-9H-fluorene, [9] 2,7-dibromo-9-(2-ethylhexyl)-9H-carbazole, [10] and benzyltrimethyl-ammonium chlorobromate [11] were prepared as described in the literature. All other reagents and solvents were used as commercially purchased without further purification.…”

Section: Materials and Measurementsmentioning

confidence: 99%

Highly Fluorescent Conjugated Copolymers Containing Dithieno[3,2‐b:2′,3′‐d]pyrrole

Zhang

Bao³

et al. 2008

Macromol. Rapid Commun.

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Three copolymers that incorporate dithieno[3,2‐b:2′,3′‐d]pyrrole with fluorene, carbazole, or pyridine have been prepared by Suzuki reaction and characterized by NMR spectroscopy and GPC. A new homopolymer of dithieno[3,2‐b:2′,3′‐d]pyrrole was also synthesized for the comparison of their structure–property relationships. Their thermal, optical, and electrochemical properties have been investigated. All the polymers exhibit good thermal stability with decomposition temperatures around 400 °C. The fluorescence quantum efficiencies of all these polymers in solution are in the range of 33.5–55.5%. The copolymers also show high film fluorescence quantum efficiencies of about 20% while the fluorescence of the homopolymer film is almost quenched.magnified image

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“…A prerequisite concerning this strategy is clearly that precursor 1 can be readily prepared on large scale. Already in 1983, Zanirato et al reported the synthesis of DTP 1 including thermolysis of an azide as the key step (method A, Scheme ) . After bromination of 3‐bromothiophene 2 to 2,3‐dibromothiophene 3 , Kumada cross‐coupling reaction of 3 and 2‐thienylmagnesium bromide gives 3‐bromo‐2,2′‐bithiophene 4 .…”

Section: Introductionmentioning

confidence: 99%

New methods for the synthesis of 4H‐dithieno[3,2‐b:2′,3′‐d]pyrrole

Förtsch

Vogt

Bäuerle

2017

J of Physical Organic Chem

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Various alternative methods for the synthesis of 4H-dithieno[3,2-b:2′,3′-d]pyrrole (DTP) starting from commercially available bromothiophene precursors are presented. Crucial steps involve the Cadogan reaction, Ullmann-type C─N couplings, or Buchwald-Hartwig-type aminations to build up the central pyrrole ring of DTP, respectively. The use of ammonia surrogates afforded the fused target heteroacene in overall yields of 33% to 63%, and the corresponding methods are applicable on large scale.

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Thermal decomposition of o-azidobithienyls

Cited by 52 publications

References 6 publications

Transistor Paint: Environmentally Stable N‐alkyldithienopyrrole and Bithiazole‐Based Copolymer Thin‐Film Transistors Show Reproducible High Mobilities without Annealing

Transistor Paint: Environmentally Stable N‐alkyldithienopyrrole and Bithiazole‐Based Copolymer Thin‐Film Transistors Show Reproducible High Mobilities without Annealing

Highly Fluorescent Conjugated Copolymers Containing Dithieno[3,2‐b:2′,3′‐d]pyrrole

New methods for the synthesis of 4H‐dithieno[3,2‐b:2′,3′‐d]pyrrole

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