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학술발표회초록보기

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제114회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Fluorescent "crowdoxidation" probes

등록일
2014년 9월 11일 09시 46분 37초
접수번호
1531
발표코드
INOR.P-264 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
발표시간
10월 15일 (수요일) 16:00~19:00
발표형식
포스터
발표분야
무기화학
저자 및
공동저자
D.G.Churchill
한국과학기술원(KAIST) 화학과, Korea
Chalcogen and organochalcogen chemistry is extremely rich. Chalcogenides provide sites of metal coordination and chemical oxidation. The chalcogens, as individual atoms, can be incorporated into the design of fluorescent (fluorogenic) molecules. This may enable novel classes of fluorophores to be produced and exploited for sensing, therapeutics and theranostics (e.g., GPx systems). The rudimentary chemistry of the chalcogens (oxides, etc) can be considered in larger or more complicated molecules, or arrays with chalcogens bearing unique positions. So far, we have produced molecules where chalcogens make up four different motifs. A simple photoinduced electron transfer (PET) donor-acceptor design can serve as the basis for rationally-designed next generation probing systems. The rotation of the “electron donor” group is critical in fluorescence properties in these systems. Our laboratory reported the first well-defined molecular probe involving chalcogen chemical oxidation as the chemical switch for fluorescence / optical changes. The benzothienyl-BODIPY serves as the PET “electron donor”. Since our original reports, other recent literature fluorophore / chromophore examples of chalcogen chemical oxidation have emerged. Our laboratory first reported a probe in which there are multiple sites of oxidation (multi-input) where a total of four oxidation sites are possible. Our laboratory first synthesized a BODIPY diselenide probe (BODIPY-o-Phenylene-Se-Se-o-Phenylene-BODIPY). Generally, it is the second diselenide probe known, but the first one that reacts with ROS. It is the second one to behave as a reversible superoxide probe. Here, the sensitivity, selectivity, time response, cell studies, stability of this sterical probe are all affirmative and decent, or excellent. An unexpected annulation product was also obtained (first chalcogen annulation product known for dipyrrins, or aryl-meso porphyrins, etc). The discovery of this molecule is an important development because the entire fluorogenic skeleton can be kept small, and the donor-acceptor moieties become blended. Synthetic molecules less than 500 Da are said to have appropriate "drug likeness." The probe exhibits “off-on” fluorescent probing at the Se or Te center, and is reversible. The structure shows large mean planarity and rigidity; the chalcogen atom is saddled halfway between the aryl ring and chromophore resulting in a red-shifted emission band relative to the parent chromophore.

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