Regioisomeric BODIPY Benzodithiophene Dyads and Triads with Tunable Red Emission as Ratiometric Temperature and Viscosity Sensors

Regioisomeric acceptor‐donor (AD) molecular rotors (p‐AD, m‐AD and m‐ADA) were synthesized and characterized, wherein dyads p‐AD and m‐AD, and triad m‐ADA contained 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) and benzodithiophene (BDT) as electron‐acceptor and electron‐donor, respectively. I...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-11, Vol.25 (65), p.14870-14880
Main Authors: Aswathy, P. R., Sharma, Sushil, Tripathi, Narendra Pratap, Sengupta, Sanchita
Format: Article
Language:English
Subjects:
aggregate induced emission
Chemistry
Chromaticity
Coupling (molecular)
Detection
dyes/pigments
Fluorescence
Light emission
Medical imaging
regioisomers
Rotors
sensors
Temperature dependence
twisted intramolecular charge transfer
Viscosity
White light
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Summary:Regioisomeric acceptor‐donor (AD) molecular rotors (p‐AD, m‐AD and m‐ADA) were synthesized and characterized, wherein dyads p‐AD and m‐AD, and triad m‐ADA contained 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) and benzodithiophene (BDT) as electron‐acceptor and electron‐donor, respectively. In all the compounds, the donor and acceptor moieties are electronically decoupled by a phenyl spacer, either through a para coupling or through a meta coupling. The dyad counterparts p‐AD and m‐AD showed distinct photophysical characteristics in which dyad p‐AD showed TICT band at ca. 654 nm characterized by a Stokes shift of ca. 150 nm and prominent solvatochromism. However, meta regioisomeric triad m‐ADA showed well‐defined aggregation in solution. Notably, because of the temperature‐tunable and solvent‐viscosity‐dependent emission, efficient ratiometric temperature sensing with positive and negative temperature coefficients and viscosity sensing was observed for all compounds. Interestingly, the fluorescence of dyad m‐AD (in 10/90 v/v THF/water) revealed a near‐white light emission with CIE chromaticity coordinates (x, y) of (0.32, 0.29). Furthermore, the fluorescence emission of p‐AD in THF at 0 °C also showed a near‐white light emission with chromaticity coordinates (x, y) of (0.34, 0.27). Such multifunctional rotors with readily tunable emission in the red region and prominent temperature‐ and viscosity‐sensing abilities are promising for sensing and bioimaging applications. Molecular sensors: Regioisomeric BODIPY‐Benzodithiophene dyads and triads show either twisted intramolecular charge transfer (TICT) with red emission or aggregation in solution. These rotors exhibit tunable red emission, pronounced temperature and viscosity sensing and near‐white light emission that are promising for bioimaging and sensing applications.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201902952