How to enhance fluorescence and two-photon properties of typical dipolar dyes in aqueous media?

European Chemistry Congress

June 16-18, 2016 Rome, Italy

Hyerim Kim, Subhankar Singha, Dokyoung Kim and Kyo Han Ahn

Pohang University of Science and Technology, Republic of Korea

Posters & Accepted Abstracts: Chem Sci J

Abstract :

The donor-acceptor (D�A) type dipolar dyes have been widely used as fluorophores in molecular probes and biological tags.1 In general, this type fluorophores emit strongly in organic solvents but poorly in aqueous media. To enhance the poor emission behaviour of dipolar dyes in aqueous media, we carried out a systematic structure variation of the donor, amino substituent of acedan which is an important two-photon dye.2 We have identified several factors that influence the emission behaviour of the diopolar dyes in aqueous media by inhibiting the liable factors for poor emission: 1,3-allylic strain, rotational freedom, and hydrogen bonding with water. This rational approach can be applied to other dipolar fluorophores, as demonstrated for naphthalimide, coumarin, and (4-nitro-2,1,3-benzoxadiazol-7-yl)amine (NBD) dyes. The new acedan and naphthalimide dyes thus allow us to obtain much brighter two-photon fluorescent images in cells and tissues than in their conventional forms. As an application of these findings, a thiol probe was synthesized based on naphthalimide dye, which showed greatly enhanced fluorescence from the widely used N,N-dimethylamino forms. The results indicated that our approach has great potential for the development of efficient dipolar dyes and fluorescence probes for studying biological systems, particularly by two-photon microscopy.

Biography :

Hyerim Kim is from Pohang University of Science and Technology, Republic of Korea
Email:ahn@postech.ac.kr