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

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

58 Citations (Scopus)

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.

Original language	English
Pages (from-to)	6386-6389
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	24
DOIs	https://doi.org/10.1021/ol503178m
Publication status	Published - Dec 19 2014
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2014 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "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",

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.",

author = "Qun Ye and Neo, \{Wei Teng\} and Cho, \{Ching Mui\} and Yang, \{Shuo Wang\} and Tingting Lin and Hui Zhou and Hong Yan and Xuehong Lu and Chunyan Chi and Jianwei Xu",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

month = dec,

day = "19",

doi = "10.1021/ol503178m",

language = "English",

volume = "16",

pages = "6386--6389",

journal = "Organic Letters",

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TY - JOUR

T1 - 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

AU - Ye, Qun

AU - Neo, Wei Teng

AU - Cho, Ching Mui

AU - Yang, Shuo Wang

AU - Lin, Tingting

AU - Zhou, Hui

AU - Yan, Hong

AU - Lu, Xuehong

AU - Chi, Chunyan

AU - Xu, Jianwei

PY - 2014/12/19

Y1 - 2014/12/19

N2 - 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.

AB - 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.

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JO - Organic Letters

JF - Organic Letters

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ER -

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

Abstract

Bibliographical note

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