Synthesis, spectra, and electron-transfer reaction of aspartic acid-functionalized water-soluble perylene bisimide in aqueous solution

ACS Appl Mater Interfaces. 2013 Apr 24;5(8):3401-7. doi: 10.1021/am4004446. Epub 2013 Apr 3.

Abstract

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 × 10(4) L cm(-1) mol(-1)) respectively in pH 7.20 HEPES buffer. Two quasi-reversible redox processes with E1/2 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 PASP(2-) 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspartic Acid / chemistry*
  • Electrolytes / chemistry
  • Electron Transport
  • Imides / chemical synthesis
  • Imides / chemistry*
  • Perylene / analogs & derivatives*
  • Perylene / chemical synthesis
  • Perylene / chemistry
  • Solubility
  • Water

Substances

  • Electrolytes
  • Imides
  • perylene bisimide
  • Water
  • Aspartic Acid
  • Perylene