Thieno[3,2-b]pyridin-5(4H)-ones 의 합성과 광화학적특성

Title
Thieno[3,2-b]pyridin-5(4H)-ones 의 합성과 광화학적특성
Alternative Title
Synthesis and Photophysical Properties of Fluorescent Thieno[3,2-b]pyridin-5(4H)-ones
Author(s)
성단비; 문보현; 박솔; 이희승; 이지훈; 이연주; 신희재; 이종석
KIOST Author(s)
Sung, Dan Bi(성단비)Lee, Hyi Seung(이희승)Lee, Jihoon(이지훈)Lee, Yeon Ju(이연주)Lee, Jong Seok(이종석)
Publication Year
2017-09-06
Abstract
Molecular fluorescence is a rapidly growing research field, which has significant applications in physical, chemical, material, and biomedical sciences. In our continued efforts to construct a small molecular library of natural product-inspired fused heterocylic ring systems, thieno[3,2-b]pyridine-5(4H)-one has been recognized as a novel fluorescent scaffold. In this presentation, we demonstrate the synthesis of highly fluorescent thieno[3,2-b]pyridine-5(4H)-one derivatives and the photophysical properties of the resulting products. The chemical synthesis of these novel fluorophores employs a series of subsequent reactions employing the Suzuki-Miyaura cross-coupling reaction, and a regioselective aza-[3 + 3] cycloaddition reaction of 3-aminothiophenes with alpha,beta-unsaturated carboxylic acids promoted by BOP ((benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate). The structure-property relationship study of this novel fluorescent scaffold revealed that the introduction of a specific functional group to the thieno[3,2-b]pyridine-5(4H)-one scaffold enables the photophysical properties to be finely tuned. Consequently, significant hypsochromic and bathochromic shifts with large Stokes shifts up to 7672 cm-1 were observed and high quantum yields up to 99% were obtained in dichloromethane. The inherent ease of chemical modification of this fluorescent scaffold would bestow a tailor-made function into a molecule of choice.[1] Valeur, B. Berberan-Santos, M. N., Molecular Fluorescence, Second Edition. Wiley: 2012.[2] Lavis, L. D. Raines, R. T., ACS Chem. Biol. 2008, 3, 142-155.[3] Lavis, L. D. Raines, R. T., ACS Chem. Biol. 2014, 9, 855-866.
URI
https://sciwatch.kiost.ac.kr/handle/2020.kiost/23848
Bibliographic Citation
제26회 ISHC(International Society of Heterocyclic Chemistry) Congress, pp.362, 2017
Publisher
ISHC (International Society of Hetrocyclic Chemistry)
Type
Conference
Language
English
Publisher
ISHC (International Society of Hetrocyclic Chemistry)
Related Researcher
Research Interests

Marine Natural Products,Organic Chemistry,해양천연물,유기화학

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