Near-IR absorbing 1,1,4,4-tetracyanobutadiene-functionalized phenothiazine sulfones

Misra, Ranjita; Man, Manju; Tewari, Nikhil P.

doi:10.1039/d3ob00361b

Cited by 6 publications

(4 citation statements)

References 35 publications

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“…The resulting onset values of oxidation and reduction were utilized for calculating the HOMO–LUMO gap and HOMO and LUMO energy levels of Fullerene-Fc . The electrochemical HOMO and LUMO energy level was determined based on the onset of oxidation and reduction potentials . Therefore, the HOMO and LUMO energy levels ( E HOMO and E LUMO ) of the Fullerene-Fc molecule can be calculated according to the following eqs (eqs to ) E HOMO = − false( E onset ( ox ) + 4.4 false) eV E LUMO = − false( E onset ( red ) + 4.4 false) eV E g = E onset ( ox ) − E onset ( red ) 0.25em eV where E onset(ox) and E onset(red) are the onsets for the oxidation and reduction potentials of Fullerene-Fc determined from the DPV experiment (vs Ag/Ag + ).…”

Section: Resultsmentioning

confidence: 99%

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Ferrocene-Functionalized Fulleropyrrolidine Derivative: A Performance Enhancer for Solid-State Electrochromic Devices

Kandpal,

Gupta,

Kumar

et al. 2024

ACS Appl. Opt. Mater.

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A custom-designed ferrocene-functionalized fulleropyrrolidine derivative Fullerene-Fc has been synthesized, which proves to be a feasible material to improve the performance of solid-state electrochromic devices. The molecule can be used as a dopant to design devices on substrates of rigid (glass) as well as flexible (PET) nature. The switching speed of devices made using poly(3hexylthiophene) and ethyl viologen could be improved to display a switching time of less than 1 s when the Fullerene-Fc molecule was added. The improvement in the performance of the electrochromic device is likely due to the solution processability of the Fullerene-Fc molecule compatible with other used electrochromic active materials, which helps to facilitate the necessary charge carriers for the redox reaction within the device. Additionally, a coloration efficiency of more than 350 cm 2 /C and cyclic stability of up to 500 s were shown by the device with a color contrast of more than 40%. Furthermore, the Fullerene-Fc molecule in the P3HT/EV device can be incorporated to fabricate an allorganic flexible device. The charge storage properties of fullerene and the redox behavior of ferrocene make it a good choice to be used as an electrochromic performance enhancer.

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Section: Resultsmentioning

confidence: 99%

“…The electrochemical HOMO and LUMO energy level was determined based on the onset of oxidation and reduction potentials. 43 Therefore, the HOMO and LUMO energy levels (E HOMO and E LUMO ) of the Fullerene-Fc molecule can be calculated according to the following eqs (eqs 1 to 3)…”

Section: Electrochemical Propertiesmentioning

confidence: 99%

Ferrocene-Functionalized Fulleropyrrolidine Derivative: A Performance Enhancer for Solid-State Electrochromic Devices

Kandpal,

Gupta,

Kumar

et al. 2024

ACS Appl. Opt. Mater.

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“…[39][40][41][42][43][44][45][46][47][48][49] Recently, our groups have reported a series of TCBD and DCNQ-based PTZ derivatives as DÀ A systems for optoelectronic applications. [50,51] The TCBD and DCNQ functionalized DÀ A small molecules and polymers have also been investigated for OPVs and NLOs. [52,53] However, despite several studies demonstrating optical and excited state electronic properties of a wide variety of DÀ A constructs in the recent past, the newly emerged sulfonamide-based push-pull systems and insight into their photophysical and electrochemical characteristics including ultrafast carrier dynamics are yet to be explored.…”

Section: Introductionmentioning

confidence: 99%

Near‐IR Capturing N‐Methylbenzene Sulfonamide‐Phenothiazine Incorporating Strong Electron Acceptor Push‐Pull Systems: Photochemical Ultrafast Carrier Dynamics

Kumar Gupta,

Das,

Misra

et al. 2024

Chemistry A European J

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Unraveling the intriguing aspects of the intramolecular charge transfer (ICT) phenomenon of multi‐modular donor‐acceptor‐based push–pull systems are of paramount importance considering their promising applications, particularly in solar energy harvesting and light‐emitting devices. Herein, a series of symmetrical and unsymmetrical donor‐acceptor chromophores 1–6, are designed and synthesized by the Corey‐Fuchs reaction via Evano’s condition followed by [2 + 2] cycloaddition retroelectrocyclic ring‐opening reaction with strong electron acceptors TCNE and TCNQ in good yields (~60–85%). The photophysical, electrochemical, and computational studies are investigated to explore the effect of incorporation of strong electron acceptors TCBD and DCNQ with phenothiazine (PTZ) donor. An additional low‐lying broad absorption band extended towards the NIR region suggests charge polarization after the introduction of the electron acceptors in both symmetrical and asymmetrical systems, leading to such strong ICT bands. Relative positions of the frontier orbitals on geometry‐optimized structures further support accessing donor‐acceptor sites responsible for the ICT transitions. Eventually, ultrafast carrier dynamics of the photoinduced species are investigated provided information about different excited states photophysical events including ICT and their associated time profiles.

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“…The π-conjugated small molecules that contain S and N atom-based heterocyclic units such as thiazoles, benzothiazoles, benzothiadiazole, carbazole, thiophene, and phenothiazines are of wide interest due to their potential applications in the field of organic light emitting diodes (OLEDs), nonlinear optics (NLO), organic photovoltaics (OPVs), and organic field-effect transistors (OFETs). − Phenothiazine is a heterocyclic compound that has a nonplanar geometry and exhibits excellent photostability and thermal stability. − 10 H -Phenothiazine is a colorless crystalline solid with an absorption maxima at 316 nm in dichloromethane. Phenothiazine can be easily functionalized by electrophilic substitution reactions at the 3 and 7 positions and nucleophilic substitution reactions at the N-position. − The high electron density and good electron donor ability of phenothiazine make it a suitable candidate to be used in various applications such as chemical sensors, photovoltaic devices, and light-emitting diodes (LEDs). , Thiophene is one of the most widely used heterocyclic compound and is widely explored as a donor material in organic solar cells (OSC) .…”

Section: Introductionmentioning

confidence: 99%

NIR-Absorbing 1,1,4,4-Tetracyanobuta-1,3-diene- and Dicyanoquinodimethane-Functionalized Donor–Acceptor Phenothiazine Derivatives: Synthesis and Characterization

Gupta,

Khan,

Misra

2023

J. Org. Chem.

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A series of symmetrical and unsymmetrical donor− acceptor type phenothiazine derivatives 1−18 were designed and synthesized via Pd-catalyzed Sonogashira cross-coupling and [2 + 2] cycloaddition−retroelectrocyclization reactions. The incorporation of cyano-based acceptors 1,1,4,4-tetracyanobutadiene (TCBD) and dicyanoquinodimethane (DCNQ) in the phenothiazine derivatives resulted in systematic variation in the photophysical, thermal, and electrochemical properties. The electronic absorption spectra of the phenothiazine derivatives with strong acceptors 2, 3, 5, 6, 8, 9, 11, 12, 14, 15, 17, and 18 show redshifted absorption as compared to phenothiazine derivatives 1, 4, 7, 10, 13, and 16 in the near-IR region due to a strong intramolecular charge transfer (ICT) transition. The electrochemical analysis of the phenothiazine derivatives 2, 3, 5,6,8,9, 11, 12,14,15,17, and 18 reveals two reduction waves at low potential due to the TCBD and DCNQ acceptors. The mono-TCBD-functionalized phenothiazine 2 shows higher thermal stability compared to other phenothiazine derivatives. The computational studies on phenothiazines 1−18 reveal the LUMO is substantially stabilized as acceptor strength increases, which lowers the HOMO−LUMO gap.

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Near-IR absorbing 1,1,4,4-tetracyanobutadiene-functionalized phenothiazine sulfones

Cited by 6 publications

References 35 publications

Ferrocene-Functionalized Fulleropyrrolidine Derivative: A Performance Enhancer for Solid-State Electrochromic Devices

Ferrocene-Functionalized Fulleropyrrolidine Derivative: A Performance Enhancer for Solid-State Electrochromic Devices

Near‐IR Capturing N‐Methylbenzene Sulfonamide‐Phenothiazine Incorporating Strong Electron Acceptor Push‐Pull Systems: Photochemical Ultrafast Carrier Dynamics

NIR-Absorbing 1,1,4,4-Tetracyanobuta-1,3-diene- and Dicyanoquinodimethane-Functionalized Donor–Acceptor Phenothiazine Derivatives: Synthesis and Characterization

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