금(I)촉매를 이용한 2-arylthieno[3,2-b]pyridine-5(4H)-ones의 합성과 vimentin 저분자 형광프로브 연구

Title
금(I)촉매를 이용한 2-arylthieno[3,2-b]pyridine-5(4H)-ones의 합성과 vimentin 저분자 형광프로브 연구
Alternative Title
Gold(I)-catalyzed synthesis of 2-arylthieno[3,2-b]pyridine-5(4H)-ones and studies toward a small-molecule fluorescent probe for vimentin
Author(s)
성단비; 문보현; 이희승; 이지훈; 이연주; 이종석
KIOST Author(s)
Sung, Dan Bi(성단비)Lee, Hyi Seung(이희승)Lee, Jihoon(이지훈)Lee, Yeon Ju(이연주)Lee, Jong Seok(이종석)
Alternative Author(s)
성단비; 이희승; 이지훈; 이연주; 이종석
Publication Year
2018-08-22
Abstract
Molecular fluorescence is a rapidly growing research field that provides an outstanding tool for nondestructive investigations in biology, biomedical science, environment and drug discovery. Moreover, there is high demand of fluorescent materials in electronic and energy industry for applications in OLED (organic light-emitting diode) and organic solar cell. Accordingly, we have witnessed remarkable advances in these fields over the last several decades and we have now an access to a variety of fluorescent scaffolds, which are commonly outsourced as the prototypes to design new fluorophores. In this poster, we describe a synthetic method for the access to a series of fluorescent thieno[3,2-b]pyridine-5(4H)-one derivatives via a gold(I)-catalyzed 6-endo-dig cycloisomerization of Nthiophen-3-yl alkynylamides. Investigation on the photophysical properties of the newly synthesized fluorophores revealed that the photophysical properties are chemically tunable by an appropriate choice of functional group on the thieno[3,2-b]pyridine-5(4H)-one scaffold (emission maxima up to 559 nm, Stokes shifts up to 197 nm, and quantum yields up to 98%). Next, our endeavor aimed at establishing a small-molecule fluorescent probe for vimentin is described which is based on the conjugate of withaferin A (a natural product originally derived from Withania somnifera) and a fluorescent thieno[3,2-b]pyridine-5(4H)-one derivative. Vimentin is aerials in electronic and energy industry for applications in OLED (organic light-emitting diode) and organic solar cell. Accordingly, we have witnessed remarkable advances in these fields over the last several decades and we have now an access to a variety of fluorescent scaffolds, which are commonly outsourced as the prototypes to design new fluorophores. In this poster, we describe a synthetic method for the access to a series of fluorescent thieno[3,2-b]pyridine-5(4H)-one derivatives via a gold(I)-catalyzed 6-endo-dig cycloisomerization of Nthiophen-3-yl alkynylamides. Investigation on the photophysical properties of the newly synthesized fluorophores revealed that the photophysical properties are chemically tunable by an appropriate choice of functional group on the thieno[3,2-b]pyridine-5(4H)-one scaffold (emission maxima up to 559 nm, Stokes shifts up to 197 nm, and quantum yields up to 98%). Next, our endeavor aimed at establishing a small-molecule fluorescent probe for vimentin is described which is based on the conjugate of withaferin A (a natural product originally derived from Withania somnifera) and a fluorescent thieno[3,2-b]pyridine-5(4H)-one derivative. Vimentin is a
URI
https://sciwatch.kiost.ac.kr/handle/2020.kiost/23163
Bibliographic Citation
American Chemical Society 256th National Meeting, pp.1 - 2, 2018
Publisher
American Chemical Society
Type
Conference
Language
English
Publisher
American Chemical Society
Related Researcher
Research Interests

Marine Natural Products,Organic Chemistry,해양천연물,유기화학

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