Ad-Hoc Functionalization of Phenothiazine Dioxide Derivatives to Achieve Blue Thermally Activated Delayed Fluorescence in Organic Nanoaggregates DOI
Chiara Montanari,

Manju Sheokand,

Alessio Cesaretti

и другие.

The Journal of Physical Chemistry C, Год журнала: 2024, Номер 128(46), С. 19688 - 19700

Опубликована: Ноя. 8, 2024

In this study, four new phenothiazine dioxide derivatives were synthesized. They functionalized with rotatable electron donor substituents characterized by different degree of rotatability (such as triphenylamine, and tetraphenylethylene) symmetrically attached to the central core. On one hand, triphenylamine- phenothiazine-based molecules exhibited efficient fluorescence in blue portion visible spectrum, consistent their modest push–pull character. other tetraphenylethylene-functionalized compound showed very low quantum yields an ultrafast nonradiative deactivation ground state via intramolecular rotations. Efficient intersystem crossing (ISC) was revealed through transient absorption experiments femtosecond nanosecond temporal resolution for triphenylamine derivatives. Organic nanoaggregates investigated fluorophores mean diameters 50–150 nm prepared water dispersion intriguingly either thermally activated delayed (TADF, triphenylamine-based dye) or aggregation-induced emission (AIE, tetraphenylethylene-based dye). Such organic nanoparticles successfully internalized human melanoma lung cancer cells, exhibiting nuclear localization imaging some cytotoxicity. TADF interestingly triphenylamine-functionalized molecule also solid state, host–guest powders where triphenylphosphine employed host matrix. This emitter holds significant potential applications third- fourth-generation OLED devices.

Язык: Английский

Roadmap for Designing Donor-π-Acceptor Fluorophores in UV-Vis and NIR Regions: Synthesis, Optical Properties and Applications DOI Creative Commons

Guliz Ersoy,

Maged Henary

Biomolecules, Год журнала: 2025, Номер 15(1), С. 119 - 119

Опубликована: Янв. 14, 2025

Donor acceptor (D-π-A) fluorophores containing a donor unit and an moiety at each end connected by conjugated linker gained attention in the last decade due to their system ease of tunability. These features make them good candidates for various applications such as bioimaging, photovoltaic devices nonlinear optical materials. Upon excitation D-π-A fluorophore, intramolecular charge transfer (ICT) occurs, it polarizes molecule resulting ‘push–pull’ system. The emission wavelengths can be altered from UV-vis NIR region modifying unit, π between them. emitting with restricted molecular rotations are used aggregation-induced (AIE). carboxylic acid cyano groups preferred applications, large surface area two photon absorbing applications. Herein, we report synthesis, properties, region.

Язык: Английский

Процитировано

1

Effects of the nature of donor substituents on the photophysical and electroluminescence properties of derivatives of perfluorobiphenyl: donor–acceptor versus donor–acceptor–donor type AIEE/TADF emitters DOI
Iryna Danyliv, Yan Danyliv, Mariia Stanitska

и другие.

Journal of Materials Chemistry C, Год журнала: 2024, Номер 12(8), С. 2911 - 2925

Опубликована: Янв. 1, 2024

The synthesis and properties of a group organic electroactive compounds based on electron-deficient perfluorobiphenyl (PFBP) are described.

Язык: Английский

Процитировано

2

Aloe Extracellular Vesicles as Carriers of Photoinducible Metabolites Exhibiting Cellular Phototoxicity DOI Creative Commons
Eleonora Calzoni, Agnese Bertoldi, Alessio Cesaretti

и другие.

Cells, Год журнала: 2024, Номер 13(22), С. 1845 - 1845

Опубликована: Ноя. 7, 2024

The growing interest in plant-origin active molecules with medicinal properties has led to a revaluation of plants the pharmaceutical field. Plant-derived extracellular vesicles (PDEVs) have emerged as promising candidates for next-generation drug delivery systems due their ability concentrate and deliver plethora bioactive molecules. These bilayer membranous vesicles, whose diameter ranges from 30 1000 nm, are released by different cell types play crucial role cross-kingdom communication between humans. Notably, PDEVs demonstrated efficacy treating various diseases, including cancer, alcoholic liver disease, inflammatory bowel disease. However, further research on plant is necessary fully understand traits purposes. This study investigates phototoxic effects (EVs)

Язык: Английский

Процитировано

2

Uncovering the substituted-position effect on excited-state evolution of benzophenone-phenothiazine dyads DOI Open Access
Jiayu Li, Sirui Yang, Ziqi Deng

и другие.

The Journal of Chemical Physics, Год журнала: 2023, Номер 159(14)

Опубликована: Окт. 11, 2023

Photofunctional materials based on donor-acceptor molecules have drawn intense attention due to their unique optical properties. Importantly, Systematic investigation of substitution effects excited-state charge transfer dynamics is a powerful approach for identifying application-relevant design principles. Here, by coupling phenothiazine (PTZ) at the ortho-, meta-, and para-positions benzene ring benzophenone (BP), three regioisomeric BP-PTZ dyads were designed understand relationship between substituted positions evolution channels. Ultrafast transient absorption used detect trace species related channels excited state. In non-polar solvent, BP-o-PTZ undergoes through-space process produce singlet charge-transfer (1CT) state, which subsequently proceeds intersystem crossing transforms into triplet (3CT) state; BP-m-PTZ experiences intramolecular (ICT) generate 1CT 3CT state (ISC) finally converts local-excited (3LE) as BP-p-PTZ, only 3LE states can be detected after ISC from On other hand, twisted ICT are generated via motion donor acceptor all or planarization PTZ unit in high polar solvents. The theoretical calculations unveil that features interaction play decisive role determining through-bond processes. Also, these results demonstrate derivatives could modified tuning dyads. This study provides deep perspective substitute-position effect donor-acceptor-type derivatives.

Язык: Английский

Процитировано

4

N^N^C-Cyclometalated rhodium(iii) complexes with isomeric pyrimidine-based ligands: unveiling the impact of isomerism on structural motifs, luminescence and cytotoxicity DOI

S. N. Vorobyeva,

Sof'ya A. Bautina,

Nikita A. Shekhovtsov

и другие.

Dalton Transactions, Год журнала: 2024, Номер 53(19), С. 8398 - 8416

Опубликована: Янв. 1, 2024

The degree of steric bulk in isomeric ligands affects structural motifs, luminescence and cytotoxicity N^N^C-cyclometallated rhodium( iii ) complexes.

Язык: Английский

Процитировано

1

Ultrafast and Quantitative FRET Sensitization of Singlet Fission in Solution‐Processable Para‐Azaquinodimethane Films DOI
Martina Alebardi,

Cristina Munzone,

Enrico Sorbelli

и другие.

Advanced Functional Materials, Год журнала: 2024, Номер 34(40)

Опубликована: Май 21, 2024

Abstract In this work, a green protocol for the synthesis of new para ‐Azaquinodimethane (pAQM) small molecules, functionalized with anisole (An) or bithiophene (TT) moieties on central unit and different alkoxy groups as lateral substituents is developed reported. The are found to strongly impact solubility processability chromophores. On other hand, steady–state time‐resolved spectroscopic results show completely spectral photophysical features An‐ TT‐ derivatives. Only TT‐compounds, nanosecond femtosecond transient absorption experiments reveal low efficiency triplet production in solution well ultrafast (≈1 ps) efficient (≈200%) singlet fission (SF) thin film. yellow An‐containing molecules instead used sensitize purple SF‐active TT‐compounds via quantitative FRET mixed films, which interestingly exhibit panchromatic extending entire visible range. With study, synergy between SF exploited at intermolecular level solid‐state first time by considering unconventional stable chromophores, opening intriguing possibilities solar energy harvesting.

Язык: Английский

Процитировано

1

Boosting the Efficiency of Red Thermally Activated Delayed Fluorescence via Conjugation Enhancement in Push‐Pull Naphthalimide Derivatives DOI Creative Commons
Chiara Montanari,

Nikhil Ji Tiwari,

Rajneesh Misra

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер 30(57)

Опубликована: Авг. 5, 2024

Abstract In this work, we synthesize a series of push–pull compounds bearing naphthalimide as the electron acceptor and tetraphenylethylene (TPE)/triphenylamine (TPA)/phenothiazine (PTZ) rich/electron donor units. These moieties are arranged in highly conjugated quadrupolar structures. The structure–property relationships investigated through joint experimental time–resolved spectroscopic computational TD–DFT study. femtosecond transient absorption fluorescence up–conversion experiments reveal ultrafast photoinduced intramolecular charge transfer. This is likely key factor leading to efficient spin–orbit CT–induced intersystem crossing for TPA– PTZ–derivatives well small singlet–to–triplet energy gap. Consequently, evidence delayed component found together with main prompt emission kinetics both solution thin film. weight Thermally Activated Delayed Fluorescence (TADF) greatly enhanced when these fluorophores used guests solid–state host matrices. TADF interestingly revealed orange–red region visible. Such long wavelength here observed surprisingly large quantum yields, thanks conjugation enhancement achieved newly synthesized structures relative previous studies. Our findings may be thus promising future development third generation TADF–based OLEDs.

Язык: Английский

Процитировано

1

Unlocking the Potential of Push‐Pull Pyridinic Photobases: Aggregation‐Induced Excited‐State Proton Transfer DOI Creative Commons
Letizia Mencaroni, Tommaso Bianconi, Maria Aurora Mancuso

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 12, 2024

The pH effect on the photophysics of three push-pull compounds bearing dimethoxytriphenylamine (TPA-OMe) as electron donor and pyridine acceptor, with different ortho-functionalization (-H, -Br, -TPA-OMe), is assessed through steady-state time-resolved spectroscopic techniques in DMSO/water mixed solutions water dispersions over a wide range. enhanced intramolecular charge transfer upon protonation pyridinic ring leads to acidochromic (from colorless yellow) acido(fluoro)chromic cyan pink) behaviours investigated compounds. In dilute DMSO/buffer mixtures these molecules exhibited low pK

Язык: Английский

Процитировано

1

Ad-Hoc Functionalization of Phenothiazine Dioxide Derivatives to Achieve Blue Thermally Activated Delayed Fluorescence in Organic Nanoaggregates DOI
Chiara Montanari,

Manju Sheokand,

Alessio Cesaretti

и другие.

The Journal of Physical Chemistry C, Год журнала: 2024, Номер 128(46), С. 19688 - 19700

Опубликована: Ноя. 8, 2024

In this study, four new phenothiazine dioxide derivatives were synthesized. They functionalized with rotatable electron donor substituents characterized by different degree of rotatability (such as triphenylamine, and tetraphenylethylene) symmetrically attached to the central core. On one hand, triphenylamine- phenothiazine-based molecules exhibited efficient fluorescence in blue portion visible spectrum, consistent their modest push–pull character. other tetraphenylethylene-functionalized compound showed very low quantum yields an ultrafast nonradiative deactivation ground state via intramolecular rotations. Efficient intersystem crossing (ISC) was revealed through transient absorption experiments femtosecond nanosecond temporal resolution for triphenylamine derivatives. Organic nanoaggregates investigated fluorophores mean diameters 50–150 nm prepared water dispersion intriguingly either thermally activated delayed (TADF, triphenylamine-based dye) or aggregation-induced emission (AIE, tetraphenylethylene-based dye). Such organic nanoparticles successfully internalized human melanoma lung cancer cells, exhibiting nuclear localization imaging some cytotoxicity. TADF interestingly triphenylamine-functionalized molecule also solid state, host–guest powders where triphenylphosphine employed host matrix. This emitter holds significant potential applications third- fourth-generation OLED devices.

Язык: Английский

Процитировано

0