Synthesis and photophysical studies of bis-enediynes as tunable fluorophores
SCIE
SCOPUS
- Title
- Synthesis and photophysical studies of bis-enediynes as tunable fluorophores
- Authors
- Hwang, GT; Son, HS; Ku, JK; Kim, BH
- Date Issued
- 2003-09-17
- Publisher
- AMER CHEMICAL SOC
- Abstract
- We have synthesized a family of bis-enediynes by two complementary Pd/Cu-catalyzed Sonogashira cross-coupling methods. One is a modified Sonogashira reaction between the TMS-protected tetraalkyne 20 (or 21) and various aromatic bromides to afford bis-enediynes 22a-d and 23a-d bearing different peripheral aryl units. The other, the reaction of bifunctional 1,1-dibromo-1-alkenes with phenylacetylene, afforded a series of bis-enediynes 24-32 bearing various core aryl groups. These chemical modifications to the core and periphery of bis-enediynes induce dramatic changes in absorption and emission spectra. Bis-enediynes 22 and 23 show a large Stokes shift of about 50-110 nm when compared to the less-conjugated bis-enediynes 20 and 21. Absorptions and emissions of bis-enediynes 25, 27-29, and 31 were red-shifted relative to those of enediyne 35. Substantial increases in fluorescence quantum yields are observed as a result of extending the T-conjugation. The emission wavelength of bis-enediynes was tailored from indigo blue to reddish-orange, suggesting that the color of emission can be tunable by modification of the core and/or peripheral units.
- Keywords
- COUPLING REACTIONS; Y-ENYNE; 1,1-DIBROMO-1-ALKENES; SUBSTITUTIONS; MACROCYCLES; STACKING; CHAIN
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/18344
- DOI
- 10.1021/JA0349148
- ISSN
- 0002-7863
- Article Type
- Article
- Citation
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 125, no. 37, page. 11241 - 11248, 2003-09-17
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