Synthesis of ultrahighly electron-deficient pyrrolo[3,4-d]pyridazine-5,7-dione by inverse electron demand Diels-Alder reaction and its application as electrochromic materials

Qun Ye; Wei Teng Neo; Ching Mui Cho; Shuo Wang Yang; Tingting Lin; Hui Zhou; Hong Yan; Xuehong Lu; Chunyan Chi; Jianwei Xu

doi:10.1021/ol503178m

Synthesis of ultrahighly electron-deficient pyrrolo[3,4-d]pyridazine-5,7-dione by inverse electron demand Diels-Alder reaction and its application as electrochromic materials

Org Lett. 2014 Dec 19;16(24):6386-9. doi: 10.1021/ol503178m. Epub 2014 Dec 1.

Authors

Qun Ye¹, Wei Teng Neo, Ching Mui Cho, Shuo Wang Yang, Tingting Lin, Hui Zhou, Hong Yan, Xuehong Lu, Chunyan Chi, Jianwei Xu

Affiliation

¹ Institute of Materials Research and Engineering, A*STAR , 3 Research Link, Singapore 117602, Singapore.

PMID: 25437510
DOI: 10.1021/ol503178m

Abstract

A new electron acceptor 6-alkylpyrrolo[3,4-d]pyridazine-5,7-dione (PPD) with a very low LUMO level has been synthesized via a challenging inverse electron demand Diels-Alder reaction between thiophene and furan-decorated tetrazine substrates and an electron-deficient 1-alkyl-1H-pyrrole-2,5-dione unit. The PPD monomer has been incorporated into a series of donor-acceptor-type conjugated polymers as electrochromic materials with good optical contrast, fast switching speed, and high coloration efficiency.