9,10-Azaboraphenanthrene-containing small molecules and conjugated polymers: synthesis and their application in chemodosimeters for the ratiometric detection of fluoride ions

The introduction of main group elements into conjugated scaffolds is emerging as a key route to novel optoelectronic materials. Herein, an efficient and versatile way to synthesize polymerizable 9,10-azaboraphenanthrene (BNP)-containing monomers by aromaticity-driven ring expansion reactions between...

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Published inChemical science (Cambridge) Vol. 9; no. 19; pp. 4444 - 4450
Main Authors Zhang, Weidong, Li, Guoping, Xu, Letian, Zhuo, Yue, Wan, Wenming, Yan, Ni, He, Gang
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.05.2018
Royal Society of Chemistry
Subjects
Aromaticity
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Detection
Fluorescence
Fluorides
Migration
Optoelectronics
Physical Sciences
Polycaprolactone
Polymers
Science & Technology
ANTIAROMATICITY
BOROLES
RING EXPANSION
B-N
ANION
PENTAPHENYLBOROLE
HETEROAROMATIC-COMPOUNDS
FIELD-EFFECT TRANSISTORS
FUNCTIONALIZED POLYSTYRENE
WATER
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Summary:The introduction of main group elements into conjugated scaffolds is emerging as a key route to novel optoelectronic materials. Herein, an efficient and versatile way to synthesize polymerizable 9,10-azaboraphenanthrene (BNP)-containing monomers by aromaticity-driven ring expansion reactions between highly antiaromatic borafluorene and azides is reported, and the corresponding conjugated small molecules and polymers are developed as well. The BNP-containing small molecules and conjugated polymers showed good air/ moisture stability and notable fluorescence properties. Addition of fluoride ions to the BNP-based small molecules and polymers induced a rapid change in the emission color from blue to green/ yellow, respectively, accompanied by strong intensity changes. The conjugated polymers showed better ratiometric sensing performance than small molecules due to the exciton migration along the conjugated chains. Further experiments showed that the sensing process is fully reversible. The films prepared by solution-deposition of BNP-based compounds in the presence of polycaprolactone also showed good ratiometric sensing for fluoride ions.
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ISSN:2041-6520
2041-6539
DOI:10.1039/c8sc00688a