title: Synthesis, spectra, and electron-transfer reaction of aspartic acid-functionalized water-soluble perylene bisimide in aqueous solution.
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.
authors.affiliation: Department of Chemistry, College of Science, Shanghai University, Shanghai 200444, China.
authors.forename: Lina
authors.initials: L
authors.lastname: Zhong
authors.forename: Feifei
authors.initials: F
authors.lastname: Xing
authors.forename: Wei
authors.initials: W
authors.lastname: Shi
authors.forename: Liuming
authors.initials: L
authors.lastname: Yan
authors.forename: Liqing
authors.initials: L
authors.lastname: Xie
authors.forename: Shourong
authors.initials: S
authors.lastname: Zhu
mesh_terms: D001224:Aspartic Acid / Q000737:chemistry*; D004573:Electrolytes / Q000737:chemistry; D004579:Electron Transport; D007094:Imides / Q000138:chemical synthesis / Q000737:chemistry*; D010569:Perylene / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D012995:Solubility; D014867:Water
chemical_list: D004573:Electrolytes; D007094:Imides; C510697:perylene bisimide; D014867:Water; D001224:Aspartic Acid; D010569:Perylene