1451070-79-3Relevant academic research and scientific papers
Improved synthesis of tetraaryl-1,4-dihydropyrrolo[3,2-b]pyrroles a promising dye for organic electronic devices: An experimental and theoretical approach
Martins, Lucas Michel?o,de Faria Vieira, Samuel,Baldacim, Gabriel Baldo,Bregadiolli, Bruna Andressa,Caraschi, José Cláudio,Batagin-Neto, Augusto,da Silva-Filho, Luiz Carlos
, p. 81 - 90 (2018)
Pyrrolo-[3,2-b]pyrroles represent a class of promising materials for application in organic electronics with interesting optoelectronic properties and great synthesis versatility, but yields obtained from varied synthetic routes are still very low, hindering their effective application for industrial purposes. In this report, we present a method for the synthesis of tetraaryl-1,4-dihydropyrrolo-[3,2-b]pyrrole derivatives by multicomponent reactions employing niobium pentachloride as a catalyst. The optical characterization of the products is also presented. Electronic structure calculations were performed to help the interpretation of the synthesis process, as well as the optical properties of the systems. Excellent yields and low reaction times were obtained, indicating that NbCl5 is an efficient catalyst for such systems. The products show promising properties for optoelectronic applications that can be adjusted by the choice of benzaldehyde derivatives used in the synthesis.
Photoinitiator with pyrrolopyrrole structure as well as preparation method and application of photoinitiator
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Paragraph 0048-0056, (2020/12/15)
The invention discloses a photoinitiator with a pyrrolopyrrole structure as well as a preparation method and application of the photoinitiator, and belongs to the technical field of photopolymerization. According to the preparation method, cyclization reaction is carried out to obtain the photoinitiator with the pyrrolopyrrole structure. Photocuring compositions can be formed by using the photoinitiator, different photoactive resin and additives, so that a photopolymerization system capable of being matched with light sources with various wavelengths can be obtained. The photoinitiator provided by the invention is novel in structure, simple and convenient in preparation method and easy to purify. The photoinitiator with the pyrrolopyrrole structure has different initiating capacities underthe irradiation of 365nm, 395nm and 470nm respectively; the efficient photopolymerization system can be obtained; and the efficient photopolymerization system can be used for preparing a three-dimensional solid product under an LED light source.
STRONGLY FLUORESCENT HETEROCYCLES AND A METHOD FOR THEIR SYNTHESIS
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Page/Page column 11; 12; 15, (2014/05/24)
This invention provides 1,4-dihydropyrrolo[3,2-b]pyrrole derivatives which can be used as strongly fluorescent compounds and a one- stage method for their synthesis from simple substrates.
Tetraaryl-, pentaaryl-, and hexaaryl-1,4-dihydropyrrolo[3,2- b ]pyrroles: Synthesis and optical properties
Krzeszewski, Maciej,Thorsted, Bjarne,Brewer, Jonathan,Gryko, Daniel T.
, p. 3119 - 3128 (2014/05/06)
Efficient conditions for the synthesis of tetra-, penta-, and hexasubstituted derivatives of 1,4-dihydropyrrolo[3,2-b]pyrrole were developed. The tetraaryl derivatives were obtained in a novel one-pot reaction among aromatic aldehydes, aromatic amines, and butane-2,3-dione. After a thorough examination of various reaction parameters (solvent, acid, temperature) p-toluenesulfonic acid was identified as the crucial catalyst. As a result, 1,4-dihydropyrrolo[3,2-b]pyrroles were obtained in the highest yields reported to date. The scope and limitation studies showed that this new method was particularly efficient for sterically hindered aldehydes (yields 45-49%). Pentaaryl- and hexaaryl-1,4-dihydropyrrolo[3,2-b]pyrroles were prepared from tetraaryl-1,4-dihydropyrrolo[3,2-b]pyrroles via direct arylation by employing both electron-poor and electron-rich aromatic and heteroaromatic haloarenes. Strategic placement of electron-withdrawing substituents at the 2-, 3-, 5-, and 6-positions produced an acceptor-donor-acceptor type fluorophore. The resulting multiply substituted heteropentalenes displayed intriguing optical properties. The relationship between the structure and photophysical properties for all compounds were directly compared and thoroughly elucidated. All synthesized products displayed strong blue fluorescence and exhibited moderate to large Stokes shifts (3000-7300 cm-1) as well as high quantum yields of fluorescence up to 88%. Two-photon absorption cross-section values measured in the near-IR region were surprisingly high (hundreds of GM), given the limited conjugation in these propeller-shaped dyes.
