Efficient Microwave‐Assisted Synthesis of Sonogashira‐Coupled Perylene Monoimide Derivatives: Impact of Electron‐Donating Groups on Optoelectronic Properties

Sharma, Vikas; Chandra, Falguni; Sahoo, Dhananjaya; Koner, Apurba Lal

doi:10.1002/ejoc.201701310

Cited by 15 publications

(10 citation statements)

References 36 publications

(27 reference statements)

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“…The absorption spectra of PMI‐CO 2 H, PMI‐acac, PMI‐PO 3 H 2 , PMI‐DPA, and PMI‐Py exhibit a structured and intense absorption band around 480–580 nm, attributed to a π–π* transition localized on the PMI moiety with similar ϵ values around 45 000 m −1 cm −1 at the maximum wavelength, in agreement with similar dyes . PMI‐NH 2 and PMI‐HQ exhibit a redshifted absorption band compared to the above dyes.…”

Section: Resultssupporting

confidence: 76%

A Comparative Investigation of the Role of the Anchoring Group on Perylene Monoimide Dyes in NiO‐Based Dye‐Sensitized Solar Cells

et al. 2020

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The anchoring group of a sensitizer may strongly affect the overall properties and stability of the resulting dye‐sensitized solar cells (DSSCs) and dye‐sensitized photoelectrosynthetic solar cells (DSPECs). The properties of seven perylene monoimide (PMI) dyes have been comprehensively studied for their immobilization on nanocrystalline NiO film. The PMI dyes differ only by the nature of the anchoring group, which are: carboxylic acid (PMI‐CO2H), phosphonic acid (PMI‐PO3H2), acetyl acetone (PMI‐acac), pyridine (PMI‐Py), aniline (PMI‐NH2), hydroxyquinoline (PMI‐HQ), and dipicolinic acid (PMI‐DPA). The dyes are investigated by cyclic voltammetry and spectroelectrochemistry and modeled by TD‐DFT quantum chemical calculations. The mode of binding of these anchoring groups is investigated by infrared spectroscopy and the stability of the binding to NiO surface is studied by desorption experiments in acidic and basic media. The phosphonic acid group is found to offer the strongest binding to the NiO surface in terms of stability and dye loading. Finally, a photophysical study by ultrafast transient absorption spectroscopy shows that all dyes inject a hole in NiO with rate constants on a subpicosecond timescale and display similar charge recombination kinetics. The photovoltaic properties of the dyes show that PMI‐HQ and PMI‐acac give the highest photovoltaic performances, owing to a lower degree of aggregation on the surface.

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Section: Resultssupporting

confidence: 76%

A Comparative Investigation of the Role of the Anchoring Group on Perylene Monoimide Dyes in NiO‐Based Dye‐Sensitized Solar Cells

et al. 2020

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“…31 Our group has also developed microwave-assisted Sonogashira coupling to make new PMI derivatives that helped to achieve higher yield of the compounds in less time compared with the traditional coupling method. 32 Similarly, PMI-Br (35) in which the bay-positions (1,6position) are functionalized with 2,5-di-tert-butylphenoxy groups while the bromo at the peri-position (9-position) of 35 is coupled with a series of groups using the Sonogashira-Hagihara cross coupling reaction protocol afforded 37, 39, 42 and 44 (as shown in Figure 8, bottom part). 11b Phenoxylation at the bay-position of halogenated PMIs is one of the most common ways to increase the solubility of perylene dyes.…”

Section: Sonogashira Couplingmentioning

confidence: 99%

“…To introduce the alkyne group at the peri-position (9-position) of PMI, PMI-Br (11) was treated with triisopropylsilyl acetylene (TIPS acetylene) in the presence of tris(dibenzylideneacetone)dipalladium(0) [Pd 2 (dba) 3 ], tris(o-tolyl)phosphine [P(o-tolyl) 3 ] and trimethylamine (Et 3 N) and followed by deprotection of TIPS acetylene to get PMI-acetylene (32). This PMI-acetylene 32 can be utilized for the further introduction of several different groups through alkyne.…”

Section: Sonogashira Couplingmentioning

confidence: 99%

Section: Synthesis Of Pmi Derivativesmentioning

confidence: 99%

“…For instance, 32 was coupled with the 9-bromo-phenanthrene using Sonogashira-Hagihara cross coupling reaction condition to get 34 in which PMI core is appended with a rigid alkynephenanthrene moiety (as shown in Figure8top part) 31. Our group has also developed microwave-assisted Sonogashira coupling to make new PMI derivatives that helped to achieve higher yield of the compounds in less time compared to the traditional coupling method 32.…”

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confidence: 99%

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Perylene Monoimide as a Versatile Fluoroprobe: The Past, Present, and Future

et al. 2021

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Perylene dyes have transcended their role as simple colorants and have been reinvigorated as functional dyes. Based on the substitution at the peri position by six-membered carboxylic imides, the perylene family is principally embellished with perylene diimides (PDIs) and perylene monoimides (PMIs). Perylene dyes are widely acclaimed and adorned on account of their phenomenal thermal, chemical, and photostability juxtaposed with their high absorption coefficient and near-unity fluorescence quantum yield. Although symmetric PDIs have always been in the limelight, its asymmetrical counterpart PMI is already rubbing shoulders, thanks to the consistent efforts of several scientific minds. Recently, there has been an upsurge in engendering PMI-based versatile organic architectures decked with intriguing photophysical properties and pertinent applications. In this review, the synthesis and photophysical features of various PMI-based derivatives along with their relevant applications in the arena of organic photovoltaics, photocatalysis, self-assembly, fluorescence sensing, and bioimaging are accrued and expounded, hoping to enlighten the less delved but engrossing realm of PMIs.

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First Approach for Structurally Unique Thieno[2,3‐e] isobenzofuran‐8(6H)‐one Tricyclic Framework of Echinothiophene and Echinothiophenegenol

2019

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The synthesis of complete carbocyclic framework present in bioactive natural products echinothiophene and echinothiophenegenol has been achieved. An acid catalysed rearrangement of isobenzofurans to angularly fused phthalides has been employed as the key step. To the best of our knowledge, this is the first synthetic approach either for the total synthesis or for the partial synthesis of the thieno[2,3‐e]isobenzofuran‐8(6H)‐one framework of the echinothiophene.

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Efficient Microwave‐Assisted Synthesis of Sonogashira‐Coupled Perylene Monoimide Derivatives: Impact of Electron‐Donating Groups on Optoelectronic Properties

Cited by 15 publications

References 36 publications

A Comparative Investigation of the Role of the Anchoring Group on Perylene Monoimide Dyes in NiO‐Based Dye‐Sensitized Solar Cells

A Comparative Investigation of the Role of the Anchoring Group on Perylene Monoimide Dyes in NiO‐Based Dye‐Sensitized Solar Cells

Perylene Monoimide as a Versatile Fluoroprobe: The Past, Present, and Future

First Approach for Structurally Unique Thieno[2,3‐e] isobenzofuran‐8(6H)‐one Tricyclic Framework of Echinothiophene and Echinothiophenegenol

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