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Aroyleneimidazophenazine: A Sensitive Probe for Detecting CN − Anion and its Solvatochromism Effect
Author(s) -
Zhao J.,
Li J.,
Li G.,
Gao J.,
Kjelleberg S. L. A.,
Loo S. C. J.,
Zhang Q.
Publication year - 2015
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2214
Subject(s) - chemistry , solvatochromism , triethylamine , fluorescence , intermolecular force , photochemistry , absorption (acoustics) , ion , crystallography , organic chemistry , molecule , physics , quantum mechanics , acoustics
A novel electron‐deficient heteroacene 15 H ‐pyrazino[2″,3″:3′,4′]pyrrolo[1′,2′:1,2]imidazo[4,5‐ b ]phenazin‐15‐one ( 1 ) has been successfully synthesized and characterized. Compound 1 can selectively recognize CN − and F − over other 10 anions including BF 4 − , PF 6 − , Cl − , SO 4 2− , NO 3 − , I − , H 2 PO 4 − , ClO 4 − , Ac − , and Br − in CHCl 3 /DMF mixed solvents with dual responses, including absorption signals and fluorescent “turn‐off” effects. CN − and F − can be distinguished by the completely quenched fluorescence (for CN − ) and partially reduced fluorescence (for F − ). Especially, compound 1 exhibits higher sensitivity to CN − than F − with the response concentration as low as 5.0 × 10 −6 mol/L. Moreover, compound 1 shows very interesting solvatochromism effect, and the CHCl 3 solution of compound 1 is sensitive to triethylamine, and its emission could change from green to red upon the addition of triethylamine, which is attributed to the n–π intermolecular charge‐transfer interaction.