Highly porous and photoluminescent pyrene-quinoxaline-derived benzimidazole-linked polymers

Altarawneh, Suha; Nahar, Lamia; Arachchige, Indika U.; El-Ballouli, Ala’a O.; Hallal, Kassem M.; Kaafarani, Bilal R.; Rabbani, Mohammad Gulam; Arvapally, Ravi K.; El‐Kaderi, Hani M.

doi:10.1039/c4ta05727a

Cited by 16 publications

(13 citation statements)

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“…Fluorescent conjugated polymers also offer many advantages in regard to simple organic fluorophores, such as amplified sensitivity and the possibility of simple introduction of desired functional groups in order to achieve better interactions with the analyte. Benzimidazole is often found as a constituent of conjugated polymers [25][26][27][28]. Optical sensing ability of benzimidazole-based fluorescent polymers is demonstrated for the detection of pH [29,30], metal ions [28] or inorganic anions [27], where benzimidazole moiety often plays a crucial role in the sensing mechanism.…”

Section: Luminescent Polymersmentioning

confidence: 99%

Optical Sensing (Nano)Materials Based on Benzimidazole Derivatives

Horak¹,

Vianello²,

Steinberg³

2019

Chemistry and Applications of Benzimidazole and Its Derivatives

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Benzimidazole derivatives are well-known biologically active substances, and therefore, they are mostly synthesised for therapeutic purposes. However, such heteroaromatic molecular systems own structure-related properties that enable a variety of applications, especially in optical science. Multifunctionality of the benzimidazole unit, such as electron accepting ability, π-bridging, chromogenic pH sensitivity/switching and metal-ion chelating properties, makes it an exceptional structural candidate for the design of optical chemical sensors and functional materials. Development of smart molecular sensors and novel (nano)materials is the emerging trend observed in materials and optical sensing science in general, in which the benzimidazole molecular systems strongly contribute and participate. In this chapter, we summarised recent advances in optical sensing (nano)materials that incorporate the benzimidazole structural moiety. Solid-state optical sensing systems, including self-assembled molecular materials based on benzimidazoles, are reviewed and discussed. In addition, immobilisation of benzimidazole derivatives onto or into various substrates and matrices, such as organic and inorganic polymers, bulk membranes and nanoparticles, utilising different chemical and physical methods, is presented and analysed.

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Section: Luminescent Polymersmentioning

confidence: 99%

Optical Sensing (Nano)Materials Based on Benzimidazole Derivatives

Horak¹,

Vianello²,

Steinberg³

2019

Chemistry and Applications of Benzimidazole and Its Derivatives

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“…[8,9,11] Very recently, we demonstrated the high oxygen evolution reaction (OER) activity in a COF arising from the nanoscopic confinement of non-noble metal hydroxides within the mesopores of a N-rich COF. [13,14] For example, benzotriazole [15,16] and benzimidazole [17] based polymers, thiofulvalene, [18] and benzothiadiazole [13a] COFs show conjugation assisted photocatalytic activity and electrical conductivity and have been used in organic electronics. [13,14] For example, benzotriazole [15,16] and benzimidazole [17] based polymers, thiofulvalene, [18] and benzothiadiazole [13a] COFs show conjugation assisted photocatalytic activity and electrical conductivity and have been used in organic electronics.…”

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confidence: 99%

“…[13,14] For example, benzotriazole [15,16] and benzimidazole [17] based polymers, thiofulvalene, [18] and benzothiadiazole [13a] COFs show conjugation assisted photocatalytic activity and electrical conductivity and have been used in organic electronics. [13][14][15][16][17][18] The band gap of such organic materials to a large extent is decided by the ordering of a face-to-face stacked columns of π-components, which is crucial to obtaining aligned conduction pathways. [13][14][15][16][17][18] The band gap of such organic materials to a large extent is decided by the ordering of a face-to-face stacked columns of π-components, which is crucial to obtaining aligned conduction pathways.…”

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confidence: 99%

Low Band Gap Benzimidazole COF Supported Ni₃N as Highly Active OER Catalyst

Nandi

Singh

Mullangi

et al. 2016

Advanced Energy Materials

205

149

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Covalent organic frameworks (COFs) have structures and morphologies closely resembling graphenes, whose modular construction permits atomiclevel manipulations. This, combined with their porous structure, makes them excellent catalyst supports. Here, the high electrocatalytic activity of a composite, formed by supporting Ni 3 N nanoparticles on a benzimidazole COF, for oxygen evolution reaction is shown. The composite oxidizes alkaline water with a near-record low overpotential of 230 mV @ 10 mA cm −2 (η 10 ). This high activity is attributed to the ability of the COF to confine the Ni 3 N nanoparticles to size regimes otherwise difficult to obtain and to its low band gap character (1.49 eV) arising from the synergy between the conducting Ni 3 N nanoparticles and the π-conjugated COF. The COF itself, as a metalfree self-standing framework, has an oxygen evolution reaction activity with η 10 of 400 mV. The periodic structure of the COF makes it serve as a matrix to disperse the catalytically active Ni 3 N nanoparticles favoring their high accessibility and thereby good charge-transport within the composite. This is evident from the amount of O 2 evolved (230 mmol h −1 g −1 ), which, to the best of our knowledge, is the highest reported. The work reveals the emergence of COF as supports for electrocatalysts.

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“…The determined λ were then used in the equation 1240/λ to calculate E g . The obtained values were within the range of the values calculated from DFT and those of other semiconducting polymers, such as liquid‐crystalline F8T2 and benzimidazole‐linked polymers …”

Section: Resultsmentioning

confidence: 99%

Synthesis, structures, and density functional theory computational study of thiophene‐containing and fluorodecorated imine‐linked polymers

Altarawneh

Jazzazi

Ababneh

et al. 2016

J of Applied Polymer Sci

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A new series of extended–conjugated and thermally stable thiophene‐containing imine‐linked polymers were synthesized via a Schiff‐base condensation reaction between aryl aldehydes and 2,6‐diaminopyridine building blocks. The backbones of the polymers were functionalized with phenyl, fluorosubstituted phenyl, thienyl, and pyridyl aromatic rings. The successful synthesis was confirmed with spectrochemical characterization techniques, including IR, 1H‐NMR, 13C‐NMR, and elemental analyses. The electronic properties of the polymers were investigated with ultraviolet–visible (UV–vis) absorption spectroscopy; the properties were collected experimentally and calculated with density functional theory (DFT) in the gas phase. The maximum absorption calculated from DFT was higher than the experimental values by about 60 nm; this was attributed to the absence of the solvent effect in the DFT case. The frontier molecular orbital ((HOMO) highest occupied molecular orbital and (LUMO) lowest unoccupied molecular orbital), optical band gap (Eg), and total energy (ET) values of the optimized structures were calculated. Apparently, there was a significant relation between the number of thiophene rings and the resulting Eg and ET values. As the number of thiophene rings in the polymer chain increased, Eg and ET decreased, and the thermal stability of the polymers increased. Eg and the absorption band edges were determined experimentally from the UV–vis and transmittance spectra, respectively. Poly(terthienyl–azomethine–pyridine–azomethine), with the highest thiophene content, had the lowest experimental and calculated Eg values (2.10 and 2.63 eV, respectively). In contrast, upon fluorination, poly[(2,5‐dithienyl–1,4‐difluorobenzene)–azomethine–pyridine–azomethine] exhibited the highest Eg (2.81 eV) and absorption band edges (2.94 eV), whereas the thermal stability decreased to 250 °C. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 44331.

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Highly porous and photoluminescent pyrene-quinoxaline-derived benzimidazole-linked polymers

Abstract: Successful incorporation of pyrene-quinoxaline building units into benzimidazole-linked polymers leads to highly porous frameworks that are semiconducting and photoluminescent.

Cited by 16 publications

References 50 publications

Optical Sensing (Nano)Materials Based on Benzimidazole Derivatives

Optical Sensing (Nano)Materials Based on Benzimidazole Derivatives

Low Band Gap Benzimidazole COF Supported Ni₃N as Highly Active OER Catalyst

Synthesis, structures, and density functional theory computational study of thiophene‐containing and fluorodecorated imine‐linked polymers

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Highly porous and photoluminescent pyrene-quinoxaline-derived benzimidazole-linked polymers

Abstract: Successful incorporation of pyrene-quinoxaline building units into benzimidazole-linked polymers leads to highly porous frameworks that are semiconducting and photoluminescent.

Cited by 16 publications

References 50 publications

Optical Sensing (Nano)Materials Based on Benzimidazole Derivatives

Optical Sensing (Nano)Materials Based on Benzimidazole Derivatives

Low Band Gap Benzimidazole COF Supported Ni3N as Highly Active OER Catalyst

Synthesis, structures, and density functional theory computational study of thiophene‐containing and fluorodecorated imine‐linked polymers

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Low Band Gap Benzimidazole COF Supported Ni₃N as Highly Active OER Catalyst