Self-Assembled Triphenylphosphonium-Conjugated Dicyanostilbene Nanoparticles and Their Fluorescence Probes for Reactive Oxygen Species

• Published in: Nanomaterials (Basel, Switzerland) Vol. 8; no. 12; p. 1034
• Main Authors: Choi, Wonjin, Lim, Na Young, Choi, Heekyoung, Seo, Moo Lyong, Ahn, Junho, Jung, Jong Hwa
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 12.12.2018; MDPI
• Subjects: Amino acids; Aqueous solutions; dicyanostilbene; Emission analysis; Emissions; Fluorescence; Fluorescent indicators; Histidine; Hydrogen peroxide; Infrared analysis; Metal ions; Mitochondria; Nanoparticles; NMR; Nuclear magnetic resonance; Organic chemistry; Probes; Quantum dots; Reactive oxygen species; ROS detection; Self-assembly; Solvents; triphenylphosphonium; Zeta potential; South Korea; Japan; self-assembly; triphenylphosphonium; dicyanostilbene; ROS detection
• ISSN: 2079-4991; 2079-4991
• DOI: 10.3390/nano8121034

We report self-assembled novel triphenylphosphonium-conjugated dicyanostilbene-based as selective fluorescence turn-on probes for 1O2 and ClO−. Mono- or di-triphenylphosphonium-conjugated dicyanostilbene derivatives 1 and 2 formed spherical structures with diameters of ca. 27 and 56.5 nm, respectively, through π-π interaction between dicyanostilbene groups. Self-assembled 1 showed strong fluorescent emission upon the addition of 1O2 and ClO− compared to other ROS (O2−, •OH, NO, TBHP, H2O2, GSH), metal ions (K+, Na+), and amino acids (cysteine and histidine). Upon addition of 1O2 and ClO−, the spherical structure of 1 changed to a fiber structure (8-nm wide; 300-nm long). Upon addition of 1O2 and ClO−, the chemical structural conversion of 1 was determined by FAB-Mass, NMR, IR and Zeta potential analysis, and the strong emission of the self-assembled 1 was due to an aggregation-induced emission enhancement. This self-assembled material was the first for selective ROS as a fluorescence turn-on probe. Thus, a nanostructure change-derived turn-on sensing strategy for 1O2 or ClO− may offer a new approach to developing methods for specific guest molecules in biological and environmental subjects.