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Aggregation Behavior and Electron‐Transfer Reaction of Dendritic Perylene Bisimide, Accompanied by the Formation of Highly Stable Anionic Radical Species
Author(s) -
Cheng Zhengmin,
Xing Feifei,
Bai Yueling,
Zhao Yongmei,
Zhu Shourong,
Li Mingxing
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700334
Subject(s) - chemistry , perylene , sodium dodecylbenzenesulfonate , monomer , photochemistry , aqueous solution , dimer , solvent , fluorescence , pulmonary surfactant , electron transfer , electron paramagnetic resonance , polymer chemistry , organic chemistry , molecule , polymer , biochemistry , physics , nuclear magnetic resonance , quantum mechanics
A polyethylene‐glycol‐functionalized perylene bisimide (PEPBI) was synthesized. Its concentration‐, solvent‐ and temperature‐dependent visible spectra were measured and its aggregation states were analyzed. PEPBI exists as an aggregate dimer in aqueous solution or predominantly as a monomer in organic solvents. The anionic surfactant sodium dodecylbenzenesulfonate (SDBS) can disperse PEPBI as a monomer in aqueous solution. The fluorescence of these solutions depends on the concentration of PEPBI and SDBS. The reduction of aggregated PEPBI with Na 2 S is slow and the monoanion radical as well as dianion species are the main forms of monomer. PEPBI exists predominantly as monomers in DMF and reacts with Na 2 S much faster. Interestingly, the anionic radical species exist in H‐aggregate form at low PEPBI concentrations and J‐aggregation occurs at high concentration. The dianion species is EPR‐silent and its color highly depends on its concentration in DMF.