BODIPY Core as Signaling Unit in Chemosensor Design

Costero, Ana M.; Parra, Margarita; Gil, Salvador; Gaviña, Pablo

doi:10.5772/intechopen.79591

Cited by 4 publications

(3 citation statements)

References 37 publications

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“…Upon the basis of these considerations, we targeted the 3-(dimethylamino)styryl-substituted boron dipyrromethene (BODIPY) dye 1 (Scheme 1). Due to their easily accessible structural modifications and remarkable photophysical properties such as photostability, high quantum yields and absorption coefficients, BODIPY chromophores have been successfully used for the development of selective and efficient chemosensors (Jeong and Yoon, 2012;Leen and Dehaen, 2012;Costero et al, 2018;Kaur and Singh, 2019). Extension of the BODIPY core conjugation by condensation with dialkylaminobenzaldehydes, as in 1, shifts the emission to higher wavelengths and allows the installation of a pH-sensitive appendix that produces distinguishable changes in fluorescence upon protonation/deprotonation (Rurack et al, 2001;Baruah et al, 2006;Yu et al, 2006;Kulyk et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

A Reconfigurable, Dual-Output INHIBIT and IMPLICATION Molecular Logic Gate

Trifoi,

Hodgson,

Dogantzis

et al. 2024

Preprint

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<p>Molecules that respond to input stimulations to produce detectable outputs can be exploited to mimic Boolean logic operators and reproduce basic arithmetic functions. We have designed a two-state fluorescent probe with tunable emission wavelength for the construction of a molecular logic gate with reconfigurable single– or dual–output capability. The system is based on a BODIPY skeleton coupled with 4-(dimethylamino)benzaldehyde. The behavior of the molecular logic gate can be easily investigated in solution with fluorescence spectroscopy, and the optical readout (fluorescence) can be monitored in one (green) or two (green and red) channels. Depending on the solvent of choice, single INHIBIT or dual INHIBIT/IMPLY logic functions can be achieved using chemical inputs (acid and base). Reconfiguration from single– to dual–output is thus made possible by operating the system in acetonitrile (single output) or toluene (dual output), respectively. The logic gate can be switched by manipulating the fluorescence emission via protonation or deprotonation, even when immobilized onto a glass substrate. At the solid state, the resulting output can be stored for extended periods of time. This feature provides two added benefits: (i) memory function and (ii) “set/reset” capability of the logic gate. Our design thus provides a proof-of-concept interface between the molecular and electronic domains.</p>

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Section: Introductionmentioning

confidence: 99%

A Reconfigurable, Dual-Output INHIBIT and IMPLICATION Molecular Logic Gate

Trifoi,

Hodgson,

Dogantzis

et al. 2024

Preprint

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show abstract

“…10,11 On the other hand, it is widely recognized that BODIPY derivatives possess valuable optical characteristics, such as intense absorption and fluorescence transitions in the visible spectral region, high molar absorption coefficients and fluorescence quantum yields, good stability and independence from pH. 12,13 Considering these facts we decided to synthesize two probes, based on BODIPY derivatives combined with Cu( ii ) (Chart 1), to detect cathinones both in water and in oral fluid. The sensing mechanism would be based on the ability of cathinones to reduce Cu( ii ) to Cu( i ) and on the different behaviour of the BODIPY core in presence of Cu( i ) or Cu( ii ).…”

Section: Introductionmentioning

confidence: 99%

Colorimetric and fluorescent detection of synthetic cathinones in oral fluid with meso-aryl BODIPYs and Cu(ii)

et al. 2022

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“…absorption coefficients, BODIPY chromophores have been successfully used for the development of selective and efficient chemosensors (Jeong and Yoon, 2012;Leen and Dehaen, 2012;Costero et al, 2018;Kaur and Singh, 2019). Extension of the BODIPY core conjugation by condensation with dialkylaminobenzaldehydes, as in 1, shifts the emission to higher wavelengths and allows the installation of a pH-sensitive appendix that produces distinguishable changes in fluorescence upon protonation/deprotonation (Rurack et al, 2001;Baruah et al, 2006;Yu et al, 2006;Kulyk et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

A Reconfigurable, Dual-Output INHIBIT and IMPLICATION Molecular Logic Gate

et al. 2020

View full text Add to dashboard Cite

Molecules that respond to input stimulations to produce detectable outputs can be exploited to mimic Boolean logic operators and reproduce basic arithmetic functions. We have designed a two-state fluorescent probe with tunable emission wavelength for the construction of a molecular logic gate with reconfigurable single-or dual-output capability. The system is based on a BODIPY skeleton coupled with 4-(dimethylamino)benzaldehyde. The behavior of the molecular logic gate can be easily investigated in solution with fluorescence spectroscopy, and the optical readout (fluorescence) can be monitored in one (green) or two (green and red) channels. Depending on the solvent of choice, single INHIBIT or dual INHIBIT/IMPLY logic functions can be achieved using chemical inputs (acid and base). Reconfiguration from single-to dual-output is thus made possible by operating the system in acetonitrile (single output) or toluene (dual output), respectively. The logic gate can be switched by manipulating the fluorescence emission via protonation or deprotonation, even when immobilized onto a glass substrate. At the solid state, the resulting output can be stored for extended periods of time. This feature provides two added benefits: (i) memory function and (ii) "set/reset" capability of the logic gate. Our design thus provides a proof-of-concept interface between the molecular and electronic domains.

show abstract

BODIPY Core as Signaling Unit in Chemosensor Design

Cited by 4 publications

References 37 publications

A Reconfigurable, Dual-Output INHIBIT and IMPLICATION Molecular Logic Gate

A Reconfigurable, Dual-Output INHIBIT and IMPLICATION Molecular Logic Gate

Colorimetric and fluorescent detection of synthetic cathinones in oral fluid with meso-aryl BODIPYs and Cu(ii)

A Reconfigurable, Dual-Output INHIBIT and IMPLICATION Molecular Logic Gate

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