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A Self‐Complementary Nucleoside: Synthesis, Solid‐State Structure, and Fluorescence Behavior
Author(s) -
Bang EunKyoung,
Won Jiyeon,
Moon Dohyun,
Lee Jin Yong,
Kim Byeang Hyean
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201000924
Subject(s) - nucleobase , stacking , fluorescence , hydrogen bond , nucleoside , molecule , crystallography , chemistry , solid state , photochemistry , stereochemistry , dna , organic chemistry , optics , physics , biochemistry
A novel self‐complementary nucleoside ( A T), featuring two complementary nucleobases linked through an ethynyl group has been synthesized. The rigid aromatic nucleobases provided A T with a pale‐blue fluorescence. Unlike most fluorescent organic molecules, nucleoside A T 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 π–π stacking of well‐organized A T 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.