A Self-Complementary Nucleoside: Synthesis, Solid-State Structure, and Fluorescence Behavior
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- Title
- A Self-Complementary Nucleoside: Synthesis, Solid-State Structure, and Fluorescence Behavior
- Authors
- Bang, EK; Won, J; Moon, D; Lee, JY; Kim, BH
- Date Issued
- 2011-08-01
- Publisher
- WILEY-BLACKWELL
- Abstract
- A novel self-complementary nucleoside (T-A), featuring two complementary nucleobases linked through an ethynyl group has been synthesized. The rigid aromatic nucleobases provided T-A with a pale-blue fluorescence. Unlike most fluorescent organic molecules, nucleoside T-A gives enhanced fluorescence in solid state. It exhibits considerably enhanced fluorescence intensity and a remarkable redshift (ca. 70 nm) in its emission maximum upon an increase in concentration or decrease in temperature as a result of the formation of aggregates stabilized through hydrogen bonding and pi-pi stacking of well-organized T-A assemblies; these interactions are also evident in the solid-state structure, determined by X-ray crystallography. DFT calculations supported the preference of such aggregation processes.
- Keywords
- aggregation; fluorescence; nucleosides; self-assembly; stacking interactions; ACID SECONDARY STRUCTURES; ORGANIC NANOPARTICLES; OPTICAL-PROPERTIES; DNA; HYDROGEN; NUCLEOBASE; ORGANIZATION; ANALOGS; SYSTEMS; QUARTET
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/17315
- DOI
- 10.1002/ASIA.201000924
- ISSN
- 1861-4728
- Article Type
- Article
- Citation
- CHEMISTRY-AN ASIAN JOURNAL, vol. 6, no. 8, page. 2048 - 2054, 2011-08-01
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