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Synthesis and Characterization of Dioxopyrrolopyrrole Derivatives Having Electron‐Withdrawing Groups
Author(s) -
Yamagata Takuya,
Kuwabara Junpei,
Kanbara Takaki
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200761
Subject(s) - chemistry , redox , homo/lumo , cyclic voltammetry , polar effect , electrochemistry , density functional theory , titration , electron transfer , redox titration , molecule , characterization (materials science) , photochemistry , combinatorial chemistry , computational chemistry , organic chemistry , nanotechnology , electrode , materials science
Abstract New dioxopyrrolopyrrole (DPP) derivatives bearing electron‐withdrawing groups have been synthesized, and their photophysical properties and redox behaviors have been examined. The electron‐accepting abilities of the derivatives were elucidated by cyclic voltammetry (CV) and redox titration analysis. The introduction of the electron‐withdrawing groups modulated the redox properties of the DPP core, and the addition of the 1,1,4,4‐tetracyanobutadiene (TCBD) moieties created a multi‐redox system. The application of TD‐DFT (time‐dependent density functional theory) revealed the HOMO and LUMO of the compounds, and the calculation results were consistent with the photophysical and electrochemical properties of the compounds. The TCBD moieties provided the dye molecule with unique physical properties such as broad charge‐transfer absorption bands and reversible multi‐redox behavior.