Synthesis, Spectra, and Electron-Transfer Reaction of Aspartic Acid-Functionalized Water-Soluble Perylene Bisimide in Aqueous Solution

• Published in: ACS applied materials & interfaces Vol. 5; no. 8; pp. 3401 - 3407
• Main Authors: Zhong, Lina, Xing, Feifei, Shi, Wei, Yan, Liuming, Xie, Liqing, Zhu, Shourong
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 24.04.2013
• Subjects: Aspartic Acid - chemistry; Electrolytes - chemistry; Electron Transport; Imides - chemical synthesis; Imides - chemistry; Perylene - analogs & derivatives; Perylene - chemical synthesis; Perylene - chemistry; Solubility; Water; perylene bisimide; electron transfer; anion radical
• ISSN: 1944-8244; 1944-8252
• DOI: 10.1021/am4004446

An aspartic acid-functionalized water-soluble perylene bisimide, N,N′-di(2-succinic acid)-perylene-3,4,9,10-tetracarboxylic bisimide (PASP) was synthesized and characterized. It has absorbance maximum A 0–0 and A 0–1 at 527 and 498 nm (ε ≈ 1.7 × 104 L cm–1 mol–1) respectively in pH 7.20 HEPES buffer. Two quasi-reversible redox processes with E 1/2 at −0.17 and −0.71 V (vs Ag/AgCl) respectively in pH 7–12.5 aqueous solutions. PASP can react with Na2S in pure aqueous solution to form monoanion radical and dianion species consecutively. PASP–• has EPR signal with g = 1.998 in aqueous solution, whereas PASP2‑ is EPR silent. The monoanion radical formation is a first-order reaction with k = 8.9 × 10–2 s–1. Dianion species formation is a zero-order reaction and the rate constant is 4.3 × 10–8 mol L–1 s–1. The presence of H2O2 greatly increases the radical formation rate constant. PASP as a two-electron transfer reagent is expected to be used in the water photolysis.