Design and synthesis of multi-stimuli responsive π-extended phenothiazine aldehydes: Solvatochromism, acidochromism, moisture detection and fluorochromic sensing of amine vapors

Kumari, Reshma; Milton, Marilyn Daisy

doi:10.1016/j.dyepig.2022.110474

Cited by 12 publications

(4 citation statements)

References 71 publications

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“…The carbonyl group incorporated as an acceptor moiety in push‐pull molecules may also form H‐bonding with the oxygen atom [103–106] . To investigate the ability of chalcones to sense the presence of trifluoroacetic acid, spectrophotometric titrations were performed in dichloromethane at 10 μM concentration.…”

Section: Resultsmentioning

confidence: 99%

“…The carbonyl group incorporated as an acceptor moiety in push-pull molecules may also form H-bonding with the oxygen atom. [103][104][105][106] To investigate the ability of chalcones to sense the presence of trifluoroacetic acid, spectrophotometric titrations were performed in dichloromethane at 10 μM concentration. Upon increasing the concentration of TFA from 0 to 18.8 mM, the absorption band corresponding to ICT (λ em = 448 nm) red shifted by 22 nm in C2, whereas the aforementioned band was red shifted by 20 nm and 16 nm upon addition of 0-18.1 mM and 0-13 mM TFA for C3 and C4, respectively (Figure S24).…”

Section: Tfa Sensing In Solution and Solid-statementioning

confidence: 99%

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Multi Stimuli Responsive Non‐Doped Red Emitting AIEE Active Phenothiazine‐Based Chalcones: Crystal Structure, Solvatochromism, Turn‐on Mechanofluorochromism and Acidochromism

Kumari

Milton

2022

Eur J Org Chem

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We report on a series of phenothiazine‐based D‐π‐A‐π‐D type cross‐conjugated non‐doped red‐emitting molecules synthesized by simple Claisen‐Schmidt condensation, which exhibit excellent AIEE phenomena through the formation of large‐sized nano‐aggregates. These thermally stable red fluorescent organic materials have low band gap energies (Eg=1.84–2.15 eV) and also display reversible mechanofluorochromism. The CIE chromaticity coordinates of red emissive ground powders were closer to the standard red‐light chromaticity coordinates. These chalcones also exhibited positive solvatochromism, and large Stokes shifts. Finally, these compounds were utilized as reversible volatile acid sensors to detect TFA in solution as well as in solid state, by virtue of the presence of electron withdrawing carbonyl oxygen, and they could detect TFA at a concentration as low as 15.8 ppm in the presence of C4.

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Section: Resultsmentioning

confidence: 99%

Section: Tfa Sensing In Solution and Solid-statementioning

confidence: 99%

Multi Stimuli Responsive Non‐Doped Red Emitting AIEE Active Phenothiazine‐Based Chalcones: Crystal Structure, Solvatochromism, Turn‐on Mechanofluorochromism and Acidochromism

Kumari

Milton

2022

Eur J Org Chem

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“…The development of multiresponsive organic substances has attracted considerable attention due to their potential applications in diverse technological areas such as optoelectronics, sensors, and bioimaging. [2][3][4][5][6][7][8][9][10][11][12][13] Various stimuli such as light, [14] mechanical force, [15][16][17] heat, and acid-base as well as metal ions and other chemicals promote structural changes in each molecule. These changes result in color changes known as photochromism, mechanochromism, piezochromism, thermochromism, acidochromism, and corresponding fluorochromism.…”

Section: Introductionmentioning

confidence: 99%

“…Structural flexibility is one of the most attractive properties of molecular luminescent substances, [1] making it possible to obtain various kinds of stimuli‐responsive and sensing molecules with fluorochromic features. The development of multi‐responsive organic substances has attracted considerable attention due to their potential applications in diverse technological areas such as optoelectronics, sensors, and bioimaging [2–13] . Various stimuli such as light, [14] mechanical force, [15–17] heat, and acid‐base as well as metal ions and other chemicals promote structural changes in each molecule.…”

Section: Introductionmentioning

confidence: 99%

C₃‐Symmetric Luminescent Diketone with Amido‐Linkage as a Polymorphic Fluorescence Emitter

Katsumi,

Kugai,

Louis

et al. 2024

Chemistry A European J

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The study introduces a novel C3‐symmetric b‐diketone compound, BTA‐D3, and its monomeric counterpart, D, with a focus on their synthetic procedure, photophysical properties and aggregation behavior. Both compounds exhibit characteristic absorption and weak fluorescence in solution, with BTA‐D3 displaying higher absorption coefficients due to its larger number of diketone units. Density Functional Theory (DFT) calculations suggest increased co‐planarity of diketone groups in BTA‐D3. A significant finding is the Aggregation‐Induced Emission (AIE) property of BTA‐D3, as its fluorescence intensity increases dramatically when exposed to specific solvent ratios. The AIE behavior is attributed to intermolecular excitonic interaction between BTA‐D3 molecules in self‐organized aggregates. We also studied fluorescence anisotropy of BTA‐D3 and D. Despite its larger size, BTA‐D3 showed reduced anisotropy values because of efficient intramolecular energy migration among three diketone units. Furthermore, BTA‐D3 demonstrates unique polymorphism, yielding different emission colors and structures depending on the solvent used. A unique approach is presented for promoting the growth of self‐organized aggregate structures via solvent evaporation, leading to distinct fluorescence properties. This research contributes to the understanding of C3‐symmetric structural molecules and provides insights into strategies for controlling molecular alignment to achieve diverse fluorescence coloration in molecular materials.

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Photophysical Properties and Photovoltaic Performance of Sensitizers with a Bipyrimidine Acceptor

Liu,

Gong,

et al. 2024

Trans. Tianjin Univ.

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Molecular engineering is a crucial strategy for improving the photovoltaic performance of dye-sensitized solar cells (DSSCs). Despite the common use of the donor–π bridge–acceptor architecture in designing sensitizers, the underlying structure–performance relationship remains not fully understood. In this study, we synthesized and characterized three sensitizers: MOTP-Pyc, MOS2P-Pyc, and MOTS2P-Pyc, all featuring a bipyrimidine acceptor. Absorption spectra, cyclic voltammetry, and transient photoluminescence spectra reveal a photo-induced electron transfer (PET) process in the excited sensitizers. Electron spin resonance spectroscopy confirmed the presence of charge-separated states. The varying donor and π-bridge structures among the three sensitizers led to differences in their conjugation effect, influencing light absorption abilities and PET processes and ultimately impacting the photovoltaic performance. Among the synthesized sensitizers, MOTP-Pyc demonstrated a DSSC efficiency of 3.04%. Introducing an additional thienothiophene block into the π-bridge improved the DSSC efficiency to 4.47% for MOTS2P-Pyc. Conversely, replacing the phenyl group with a thienothiophene block reduced DSSC efficiency to 2.14% for MOS2P-Pyc. Given the proton-accepting ability of the bipyrimidine module, we treated the dye-sensitized TiO2 photoanodes with hydroiodic acid (HI), significantly broadening the light absorption range. This treatment greatly enhanced the short-circuit current density of DSSCs owing to the enhanced electron-withdrawing ability of the acceptor. Consequently, the HI-treated MOTS2P-Pyc-based DSSCs achieved the highest power conversion efficiency of 7.12%, comparable to that of the N719 dye at 7.09%. This work reveals the positive role of bipyrimidine in the design of organic sensitizers for DSSC applications.

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Design and synthesis of multi-stimuli responsive π-extended phenothiazine aldehydes: Solvatochromism, acidochromism, moisture detection and fluorochromic sensing of amine vapors

Cited by 12 publications

References 71 publications

Multi Stimuli Responsive Non‐Doped Red Emitting AIEE Active Phenothiazine‐Based Chalcones: Crystal Structure, Solvatochromism, Turn‐on Mechanofluorochromism and Acidochromism

Multi Stimuli Responsive Non‐Doped Red Emitting AIEE Active Phenothiazine‐Based Chalcones: Crystal Structure, Solvatochromism, Turn‐on Mechanofluorochromism and Acidochromism

C₃‐Symmetric Luminescent Diketone with Amido‐Linkage as a Polymorphic Fluorescence Emitter

Photophysical Properties and Photovoltaic Performance of Sensitizers with a Bipyrimidine Acceptor

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Design and synthesis of multi-stimuli responsive π-extended phenothiazine aldehydes: Solvatochromism, acidochromism, moisture detection and fluorochromic sensing of amine vapors

Cited by 12 publications

References 71 publications

Multi Stimuli Responsive Non‐Doped Red Emitting AIEE Active Phenothiazine‐Based Chalcones: Crystal Structure, Solvatochromism, Turn‐on Mechanofluorochromism and Acidochromism

Multi Stimuli Responsive Non‐Doped Red Emitting AIEE Active Phenothiazine‐Based Chalcones: Crystal Structure, Solvatochromism, Turn‐on Mechanofluorochromism and Acidochromism

C3‐Symmetric Luminescent Diketone with Amido‐Linkage as a Polymorphic Fluorescence Emitter

Photophysical Properties and Photovoltaic Performance of Sensitizers with a Bipyrimidine Acceptor

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C₃‐Symmetric Luminescent Diketone with Amido‐Linkage as a Polymorphic Fluorescence Emitter