A triazine-based BODIPY trimer as a molecular viscometer

Raut, Sangram; Kimball, Joseph; Fudala, Rafał; Bora, Ilkay; Chib, Rahul; Jaafari, Hana; Castillo, Marlius; Smith, Nicholas W.; Gryczyński, Ignacy; Dzyuba, Sergei V.; Gryczyński, Zygmunt

doi:10.1039/c5cp07214j

Cited by 28 publications

(18 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…According to this analysis (Figure S21, Table S10), p ‐AD , m ‐AD , p ‐ADA , and m ‐ADA showed viscosity sensitivity ( x ) of 0.09, 0.23, 0.12, 0.31, respectively. Typical values of slopes ( x ) for rotors vary from 0.1 to 1.4 for different rotors . Thus, among the four compounds, m ‐ADA is most sensitive to viscosity and shows the best viscosity sensing ( x= 0.31) characteristics.…”

Section: Resultsmentioning

confidence: 99%

“…[17] TICT rotors are promising viscosity probes because they exhibit emission enhancement due to restricted intramolecular rotationinsolvents of increasingv iscosity. [10,11,[18][19][20] Examples of ratiometric temperature and/or viscosity [8,11] sensors based on TICT rotors involvef luorophores such as tetraphenylethylenes (TPE), [4] indocyanines, [10,21] porphyrins, [22] 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY), [23][24][25][26][27] arylboranes, [28] N,N-dimethylaniline based compounds, [29] and many others. [25,26,[30][31][32][33][34][35] Luminescent thermometers based on molecular rotors are being intensively investigated for temperature sensing of cellular microenviron-ments as well as of microfluidic devices.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

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

Aswathy

Sharma

Tripathi

et al. 2019

Chemistry A European J

View full text Add to dashboard Cite

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.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Aswathy

Sharma

Tripathi

et al. 2019

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…Therefore, HC‐ 1 functions as molecular rotor that is responsive to viscosity. According to Forster‐Hoffmann theory, the slope B relates to the nature of the molecular rotor with a B value ∼0.6 for a perfect rotor . Fitting of our experimental data revealed a B value of ∼0.46 for HC‐ 1 (Figure B).…”

Section: Resultsmentioning

confidence: 99%

Facile Synthesis of Highly Sensitive, Red-Emitting, Fluorogenic Dye for Microviscosity and Mitochondrial Imaging in Embryonic Stem Cells

et al. 2017

View full text Add to dashboard Cite

Bright, sensitive fluorescent probes that respond to changes in the cellular microenvironment are extremely valuable for imaging cellular dynamics. We report a simple, one-step synthesis of a new hemicaynine (HC-1) dye as a sensitive, redemitting (l max -610 nm) fluorogenic probe for micro-viscosity and local order in diverse environments, including live cells. HC-1 responds to increasing micro-viscosity through changes in fluorescence intensity and lifetime, and is sensitive enough to report dynamic micellar self-assembly. While HC-1 shows properties of a molecular 'rotor', time-dependent density functional theoretical analysis reveals that in HC-1, an inhibition of photo-isomerization in viscous environment is the likely cause of fluorescence enhancement. HC-1 localizes to mitochondria in live cells and responds to mitochondrial ordering through a significant increase in fluorescence. Strikingly, we show that HC-1 is also a sensitive probe for the spatial heterogeneity of mitochondrial organization in embryonic stem cells as well as dynamic remodeling of the mitochondria in early-differentiated cells.

show abstract

“…BODIPY-trimeric FMRs as viscosity sensors have also been reported ( Figure 15). [25] To maximize the light-harvestinga bility of the molecular rotor, the triazenec ore was used as al inker in BODIPY-trimeric FMRs. These BODIPY-trimeric FMRs exhibitedm olar absorption coefficients 3times higher ( % 200,000 m À1 cm À1 )t han that of dimeric FMRs, andi ts FL quantumy ield and lifetime increased with increasingv iscosity.…”

Section: High Fluorescence Contrastmentioning

confidence: 99%

Fluorescent Molecular Rotors for Viscosity Sensors

Lee

Heo

Woo

et al. 2018

Chemistry A European J

199

117

View full text Add to dashboard Cite

Fluorescent molecular rotors (FMRs) can act as viscosity sensors in various media including subcellular organelles and microfluidic channels. In FMRs, the rotation of rotators connected to a fluorescent π-conjugated bridge is suppressed by increasing environmental viscosity, resulting in increasing fluorescence (FL) intensity. In this minireview, we describe recently developed FMRs including push-pull type π-conjugated chromophores, meso-phenyl (borondipyrromethene) (BODIPY) derivatives, dioxaborine derivatives, cyanine derivatives, and porphyrin derivatives whose FL mechanism is viscosity-responsive. In addition, FMR design strategies for addressing various issues (e.g., obtaining high FL contrast, internal FL references, and FL intensity-contrast trade-off) and their biological and microfluidic applications are also discussed.

show abstract

A triazine-based BODIPY trimer as a molecular viscometer

Abstract: Photophysical behaviour of a novel trimeric BODIPY rotor with a high extinction coefficient is reported.

Cited by 28 publications

References 48 publications

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

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

Facile Synthesis of Highly Sensitive, Red-Emitting, Fluorogenic Dye for Microviscosity and Mitochondrial Imaging in Embryonic Stem Cells

Fluorescent Molecular Rotors for Viscosity Sensors

Contact Info

Product

Resources

About