Impact of ethynylene linkers on the optical and electrochemical properties of benzothiadiazole based alternate conjugated polymers

Al-Azzawi, Ahmed; Aziz, Shujahadeen B.; Iraqi, Ahmed; Murad, Ary R.; Abdulwahid, Rebar T.; Alshehri, Saad M.; Ahamad, Tansir

doi:10.1016/j.arabjc.2021.103320

Cited by 7 publications

(6 citation statements)

References 33 publications

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“…These polymers were only obtained in their toluene fractions. It was speculated that the incorporation of the ethynylene and ethynylene–thiophene spacers over the polymer chains results in a decrease in the torsion angle between alternate units along polymer chains, leading to the aggregation of polymer chains as a result of their coplanar geometry [ 37 , 38 ]. This then limits the accessibility to soluble high molecular weight polymers.…”

Section: Resultsmentioning

confidence: 99%

“…Meanwhile, the M n and M w of its counterpart PFDTNT are 41,100 and 79,500 Da, respectively. It is hypothesized that the presence of ethynylene-spacers facilitates π–π interchain stacking and planarization, leading to reduced M n and M w values obtained for PFDENT relative to those of its counterpart PFDTNT [ 38 ].…”

Section: Resultsmentioning

confidence: 99%

“…As a result, the absorption maxima for PFDENT is red-shifted compared to its analogue PFDTNT [ 39 ]. This may extend the absorption spectrum of the synthesized polymer, although the presence of acetylene units may localize the π-electron wave function on ethynylene spacers; therefore, this decreases the electronic delocalization between the electron acceptor and the donor segments [ 25 , 38 ].…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Characterization of Polymers Containing Ethynylene and Ethynylene-Thiophene Based Alternating Polymers Containing 2,1,3-Linked Naphthothiadiazole Units as Acceptor Linked with Fluorine as Donor: Electrochemical and Spectroscopic Studies

et al. 2022

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The effect of ethynylene or ethynylene–thiophene spacers on the band gap of alternating polymers, containing 4,9-naphthothiadiazole units as an acceptor and 2,7-linked fluorene repeat units as a donor, were investigated. The Sonogashira coupling reaction was employed to prepare the two novel copolymers, namely ((9,9-dioctyl-fluorene)-2,7-diethynylene-alt-4,9-2,1,3-naphthothiadiazole (PFDENT) and poly(5,5’-(9,9-dioctyl-fluorene-2,7-diyl)bis(ethynyl-2-thienyl)-alt-4,9-(2,1,3-naphthothiadiazole) (PFDTENT). The optical, electrochemical and thermal properties of the two obtained polymers were widely investigated and compared. Both resulting polymers showed low solubility in common organic solvents and moderate molecular weights. It is believed that the introduction of acetylene linkers rather than acetylene–thiophene spacers on the polymer chains reduces the steric hindrance between the donor and acceptor units which leads to the adoption of more planar structures of polymeric chains, resulting in decreased molecular weights of the resulting conjugated polymers. Thus, both ethynylene-based polymers and ethynylene–thiophene-based polymers showed red-shifted absorption maxima compared to their counterpart (thiophene-based polymer), owing to the adoption of more planar structures. Optical studies revealed that the new ethynylene and ethynylene–thiophene-based polymers displayed low band gaps compared to their thiophene analogue polymer PFDTNT. Both resulting polymers showed good thermal stability. X-ray diffraction (XRD) patterns of both polymers revealed that PFDENT and PFDTENT possessed an amorphous nature in solid state.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Synthesis and Characterization of Polymers Containing Ethynylene and Ethynylene-Thiophene Based Alternating Polymers Containing 2,1,3-Linked Naphthothiadiazole Units as Acceptor Linked with Fluorine as Donor: Electrochemical and Spectroscopic Studies

et al. 2022

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“…A broad diffraction peak at 2𝜃 ∼20 o is observed in the powder X-ray diffraction patterns (Figure S15, Supporting Information). This could be attributed to the 𝜋-𝜋 stacking of the aromatic moieties in the materials, [44,45] reflecting the amorphous nature of these materials. The morphologies were visualized with scanning electron microscopy, where all these materials are found to be irregular particles (Figure S16, Supporting Information).…”

Section: Synthesis and Characterization Of Materialsmentioning

confidence: 99%

Ultra‐Selective and Efficient Static/Dynamic Palladium Capture from Highly Acidic Solution with Robust Macrocycle‐Based Polymers

Wang

et al. 2023

Adv Funct Materials

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The capture of palladium from spent nuclear fuel is crucial for the sustainable development of nuclear energy and resource recovery. One of the most challenging issues in this direction is the survival of adsorbents under extreme reprocessing conditions such as strongly acidic media and high radiation fields while still maintaining high extraction ability and selectivity. Herein, an approach to addressing this issue is reported by incorporating macrocycle into nitrogen‐rich covalent organic polymers (COPs). Dramatically outperforming current adsorbing materials, pillar[5]arene‐based COPs with pyridyl and triazolyl functionalities display record adsorption capacity for Pd(II) at 3 M HNO3 (403 mg g−1), extraordinary stability under 500 kGy gamma irradiation, and ultra‐high selectivity toward Pd(II) over both 17 coexisting cations and six anions. In particular, the material P5COP‐m‐BPT with the best performance also shows remarkable dynamic adsorption efficiency for Pd(II). This study not only provides a strategy to enhance all‐sided adsorption performance in palladium separation with nitrogen‐rich COPs materials but also demonstrates the superiority of customizing advanced materials with macrocycles.

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“…This effect remains a challenging factor in improving the efficiency of D–A conjugated polymers. 51 An ethynylene linker has been employed along the conjugated polymer backbone between the donor and acceptor units in order to enhance the rigidity and packing of the polymer chains. The introduction of an ethynylene moiety, which is a weak electron-withdrawing unit, into the main chain of conjugated polymers generally enlarges their electronic bandgaps and lowers their HOMO energy levels.…”

Section: Introductionmentioning

confidence: 99%

High-performance, low-voltage organic field-effect transistors using thieno[3,2-b]thiophene and benzothiadiazole co-polymers

et al. 2022

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Impact of ethynylene linkers on the optical and electrochemical properties of benzothiadiazole based alternate conjugated polymers

Cited by 7 publications

References 33 publications

Synthesis and Characterization of Polymers Containing Ethynylene and Ethynylene-Thiophene Based Alternating Polymers Containing 2,1,3-Linked Naphthothiadiazole Units as Acceptor Linked with Fluorine as Donor: Electrochemical and Spectroscopic Studies

Synthesis and Characterization of Polymers Containing Ethynylene and Ethynylene-Thiophene Based Alternating Polymers Containing 2,1,3-Linked Naphthothiadiazole Units as Acceptor Linked with Fluorine as Donor: Electrochemical and Spectroscopic Studies

Ultra‐Selective and Efficient Static/Dynamic Palladium Capture from Highly Acidic Solution with Robust Macrocycle‐Based Polymers

High-performance, low-voltage organic field-effect transistors using thieno[3,2-b]thiophene and benzothiadiazole co-polymers

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