期刊
CHEMICAL SCIENCE
卷 6, 期 7, 页码 4335-4342出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5sc01076d
关键词
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资金
- Ministry of Health Welfare [HI13C1378]
- Global Research Program through the National Research Foundation (NRF) [2014K1A1A2064569]
- NRF of Korea (MSIP) [2007-0056330]
- Institute for Basic Science (IBS) in Korea
- NRF [2014R1A2A1A12067510]
- Korea government (MEST)
- NRF of Korea (MEST) [2012-0009380]
- Ministry of Science, ICT & Future Planning of Korea
The donor-acceptor (D-A) type dipolar fluorophores, an important class of luminescent dyes with two-photon absorption behaviour, generally emit strongly in organic solvents but poorly in aqueous media. To understand and enhance the poor emission behaviour of dipolar dyes in aqueous media, we undertake a rational approach that includes a systematic structure variation of the donor, amino substituent of acedan, an important two-photon dye. We identify several factors that influence the emission behaviour of the dipolar dyes in aqueous media through computational and photophysical studies on new acedan derivatives. As a result, we can make acedan dyes emit bright fluorescence under one-and two-photon excitation in aqueous media by suppressing the liable factors for poor emission: 1,3-allylic strain, rotational freedom, and hydrogen bonding with water. We also validate that these findings can be generally extended 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 is synthesized based on a new naphthalimide dye, which shows greatly enhanced fluorescence from the widely used N,N-dimethyl analogue. The results disclosed here provide essential guidelines for the development of efficient dipolar dyes and fluorescence probes for studying biological systems, particularly by two-photon microscopy.
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