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Phys Chem Chem Phys. 2015 Apr 14;17(14):9167-72. doi: 10.1039/c5cp00207a. Epub 2015 Mar 11.

Aqueous self-assembly of a charged BODIPY amphiphile via nucleation-growth mechanism.

Physical chemistry chemical physics : PCCP

Le Yang, Gang Fan, Xiangkui Ren, Lingyun Zhao, Jingkang Wang, Zhijian Chen

Affiliations

  1. School of Chemical Engineering and Technology, and Collaborative Innovation Center of Chemical Science and Chemical Engineering (Tianjin), Tianjin University, Tianjin, 300072, China. [email protected].

PMID: 25759290 DOI: 10.1039/c5cp00207a

Abstract

A new amphiphilic boron-dipyrromethene (BODIPY) dye 1 with a hydrophobic wedge at the meso-position and two hydrophilic cationic moieties at boron was synthesized. Temperature- and concentration-dependent UV/Vis spectroscopic studies in water were conducted to explore the self-assembly process of the dye. Detailed analysis of the data using two different models (developed by Van der Schoot et al. and Goldstein et al. respectively) for cooperative supramolecular polymerization indicates distinctly a nucleation-growth mechanism of the aggregation of dye 1 and the nucleus size (ca. 12-18 molecules) and a cooperativity factor (ca. 0.01) could be derived. Further investigation by transmission electron microscopy, scanning confocal microscopy, and X-ray diffraction revealed a unique vesicular morphology of the aggregates with multilamellar wall structure. Meanwhile, these dye vesicles exhibit unique optical characteristics, i.e. red-shifted sharp absorption band, narrowed emission linewidth, and increase in fluorescence quantum yield, as compared with the monomeric dye.

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