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ۼ : 15-05-27 16:59
[15.05]ȱѱ -A Structural Remedy toward Bright Dipolar Fluorophores in Aqueous Media
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ȸ : 1,779  

 

A Structural Remedy toward Bright Dipolar Fluorophores in Aqueous Media 

  

Subhankar Singha, Dokyoung Kim, Basab Roy, Sunderraman Sambasivan, Hyunsoo Moon, Alla Sreenivasa Rao, Jin Yong Kim, Taiha Joo, Jae Woo Park, Young Min Rhee, Taejun Wang, Ki Hean Kim, Youn Ho Shin, Junyang Jung, and Kyo Han Ahn.

 

The donoracceptor (DA) type dipolar fluorophores, an important class of luminescent dyes with two-photon absorption property, generally emit strongly in organic solvent 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 twophoton excitation in aqueous media by suppressing of 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 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. 

  

ְ ް Ǿ ü ̱ ɷ, ɷ ( 󿡼 ɷ) Ư ִ߿ ˷ִ. ̱ ȭ ַ Ǵ Ƽܵ ϴ üν, 󿡼 ⸦ ִ. 츮 Ƽ ְ κ ƹ پϰ ٲν 󿡼 ⸦ ų ִ ҿ Ͽ Ͽ. 츮 Ư ִ Ҹ ׸ Ͽ. 츮 󿡼 ϱ ̱ Ͽ ̴ Ƽ ü ϴµ Ͽ. 츮 ã Ҵ 1,3 ˸ Ʈ, ȸ , ̸ ҵ Ƽ Ӹ ƴ϶ Ż̵̹, ,  Ǿ ȮϿ. Chem. Sci. 5 16 Ǿ.


 
 

Total 73
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49 [15.05]ȱѱ -A Structural Remedy toward Bright Dipolar Fluorophores in Aqueous Media 05-27 1780
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