Improved synthesis of tetraary1-1,4-dihydropyrrolo[3,2-b]pyrroles a promising dye for organic electronic devices: An experimental and theoretical approach

Author(s)

Martins, Lucas Michelao ^[1] ; Vieira, Samuel de Faria ^[2] ; Baldacim, Gabriel Baldo ^[1] ; Bregadiolli, Bruna Andressa ^[1] ; Caraschi, Jose Claudio ^[2] ; Batagin-Neto, Augusto ^[2] ; da Silva-Filho, Luiz Carlos ^[1]

Affiliation

^[1] Sao Paulo State Univ UNESP, Dept Chem, Lab Organ Synth & Proc, Sch Sci, Ave Engn Luiz Edmundo Carrijo Coube 14-01, BR-17033360 Bauru, SP - Brazil

^[2] Sao Paulo State Univ UNESP, Campus Itapeva, Rua Geraldo Alckmin 519, BR-18409010 Itapeva, SP - Brazil

• Document type: Journal article
• Source: DYES AND PIGMENTS; v. 148, p. 81-90, JAN 2018.
• Web of Science Citations: 9

Abstract

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 tetraary1-1,4-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. (C) 2017 Elsevier Ltd. All rights reserved. (AU)

• FAPESP's process: 16/01599-1 - Studies about the use of NbCl5 in multicomponent reactions for the synthesis of organic dyes
• Grantee: Luiz Carlos da Silva Filho
• Support Opportunities: Regular Research Grants