title: Excitation-dependent visible fluorescence in decameric nanoparticles with monoacylglycerol cluster chromophores.
abstract: Organic fluorescent nanoparticles, excitation-dependent photoluminescence, hydrogen-bonded clusters and lysobisphosphatidic acid are four interesting individual topics in materials and biological sciences. They have attracted much attention not only because of their unique properties and important applications, but also because the nature of their intriguing phenomena remained unclear. Here we report a new type of organic fluorescent nanoparticles with intense blue and excitation-dependent visible fluorescence in the range of 410-620 nm. The nanoparticles are composed of ten bis(monoacylglycerol)bisphenol-A molecules and the self-assembly occurs only in elevated concentrations of 2-monoacylglycerol via radical-catalysed 3,2-acyl migration from 3-monoacylglycerol in neat conditions. The excitation-dependent fluorescence behaviour is caused by chromophores composed of hydrogen-bonded monoacylglycerol clusters, which are linked by an extensive hydrogen-bonding network between the ester carbonyl groups and the protons of the alcohols with collective proton motion and HO···C=O (n→π) interactions.
authors: Department of Chemistry, National Kaohsiung Normal University, No. 62, Shenjhong Road, Yanchao, Kaohsiung 82444, Taiwan. kmlee@nknu.edu.tw
authors: Kwang-Ming
authors: KM
authors: Lee
authors: Wan-Yin
authors: WY
authors: Cheng
authors: Cheng-Yu
authors: CY
authors: Chen
authors: Jing-Jong
authors: JJ
authors: Shyue
authors: Chih-Chun
authors: CC
authors: Nieh
authors: Chen-Fu
authors: CF
authors: Chou
authors: Jia-Rong
authors: JR
authors: Lee
authors: Ya-Yun
authors: YY
authors: Lee
authors: Chih-Yang
authors: CY
authors: Cheng
authors: Sarah Y
authors: SY
authors: Chang
authors: Thomas C
authors: TC
authors: Yang
authors: Mei-Ching
authors: MC
authors: Cheng
authors: Bi-Yun
authors: BY
authors: Lin
mesh_terms: D001559:Benzhydryl Compounds / Q000737:chemistry; D016000:Cluster Analysis; D005456:Fluorescent Dyes / Q000737:chemistry*; D006860:Hydrogen Bonding; D008246:Lysophospholipids / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D050178:Monoglycerides / Q000138:chemical synthesis / Q000737:chemistry*; D053758:Nanoparticles / Q000737:chemistry* / Q000648:ultrastructure; D010636:Phenols / Q000737:chemistry; D011108:Polymers / Q000737:chemistry; D011789:Quantum Theory; D013050:Spectrometry, Fluorescence; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D000098826:Bisphenol A Compounds
chemical_list: D001559:Benzhydryl Compounds; D005456:Fluorescent Dyes; D008246:Lysophospholipids; D050178:Monoglycerides; D010636:Phenols; D011108:Polymers; C012786:bis(monoacylglyceryl)phosphate; C006780:bisphenol A; D000098826:Bisphenol A Compounds