An alternating copolymer of fluorene donor and quinoxaline acceptor versus a terpolymer consisting of fluorene, quinoxaline and benzothiadiazole building units: synthesis and characterization

Gedefaw, Desta Antenehe; Ma, Zaifei; Mulugeta, Endale; Zhao, Yang; Zhang, Fengling; Andersson, Mats R.; Mammo, Wendimagegn

doi:10.1007/s00289-015-1541-y

Cited by 6 publications

(4 citation statements)

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“…Similar electron transfer processes have been observed in fluorene-quinoxaline push-pull conjugated polymers. 49,50 ■ CONCLUSIONS In the multicomponent MOFs investigated here, the truxene ligand can be viewed as a cyclic trimer of fluorene. The architecture of the MUF-7 and MUF-77 frameworks aids in the longevity of these radicals.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Irradiation of these frameworks at 405 nm thus induces electron transfer from the truxene-based hmtt ligands to the bdc-quin ligands to generate a truxene radical cation and a pyrazine radical anion. Similar electron transfer processes have been observed in fluorene-quinoxaline push-pull conjugated polymers. , …”

Section: Resultsmentioning

confidence: 99%

“…Similar electron transfer processes have been observed in fluorene-quinoxaline push-pull conjugated polymers. 49 , 50 …”

Section: Resultsmentioning

confidence: 99%

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Photoinduced Electron Transfer in Multicomponent Truxene-Quinoxaline Metal–Organic Frameworks

et al. 2022

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Metal−organic frameworks (MOFs) can respond to light in a number of interesting ways. Photochromism is observed when a structural change to the framework is induced by the absorption of light, which results in a color change. In this work, we show that introducing quinoxaline ligands to MUF-7 and MUF-77 (MUF = Massey University Framework) produces photochromic MOFs that change color from yellow to red upon the absorption of 405 nm light. This photochromism is observed only when the quinoxaline units are incorporated into the framework and not for the standalone ligands in the solid state. Electron paramagnetic resonance (EPR) spectroscopy shows that organic radicals form upon irradiation of the MOFs. The EPR signal intensities and longevity depend on the precise structural details of the ligand and framework. The photogenerated radicals are stable for long periods in the dark but can be switched back to the diamagnetic state by exposure to visible light. Single-crystal X-ray diffraction analysis reveals bond length changes upon irradiation that are consistent with electron transfer. The multicomponent nature of these frameworks allows the photochromism to emerge by allowing through-space electron transfer, precisely positioning the framework building blocks, and tolerating functional group modifications to the ligands.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Photoinduced Electron Transfer in Multicomponent Truxene-Quinoxaline Metal–Organic Frameworks

et al. 2022

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“…Suzuki coupling reaction of benzothiadiazole (25%), quinoxaline (25%), and fluorene (50%) based monomers yielded a random terpolymer (P49) (Figure 6). A reference polymer based on quinoxaline and fluorene monomers was also reported (P48) (Gedefaw et al, 2016a). P49 has revealed an extended and broad optical absorption spectrum, showing the role of the third component (benzothiadiazole) in fine tuning the optical absorption.…”

Section: Quinoxaline Ring Based Polymersmentioning

confidence: 99%

Recent Advances in the Synthesis of Electron Donor Conjugated Terpolymers for Solar Cell Applications

2020

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The synthesis of donor (D)-acceptor (A) polymers using structurally elaborated monomers is an active research field. Some of the challenges with the use of alternating D-A polymers for photovoltaic applications are the relatively narrow absorption widths, the presence an absorption valleys in the visible region, unoptimized molecular energy levels and even lack of compatibility of the polymers with the common acceptors. The synthesis and characterization of polymers consisting of multiple chromophores (random and regular terpolymers) with complementing properties is currently gaining momentum in order to delicately optimize properties of polymers. A random terpolymer can either be of a system composed of one donor and two acceptors [(D-A1)-ran-(D-A2)] or a one acceptor and two donor segments [(D1-A)-ran-(D2-A)] incorporated in the polymer backbone. By varying the composition of the monomers in the feed of the polymerization reaction, the properties of the resulting terpolymers can be carefully optimized. Using this strategy, many materials with desired properties have been developed and power conversion efficiency (PCE) surpassing 14% in a single layer bulk heterojunction (BHJ) solar cell device have been reported. This review summarizes the most recent advances made in the development of electron donor terpolymers for organic photovoltaics (OPVs). The properties of the terpolymers are compared with their respective reference polymer.

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Recent Development of Quinoxaline Based Polymers/Small Molecules for Organic Photovoltaics

Gedefaw

Prosa

Bolognesi

et al. 2017

Advanced Energy Materials

134

122

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Among the various molecular designs developed for the synthesis of conjugated polymers and small molecules for optoelectronic applications, the donor: acceptor (D–A) approach is the most widely explored method over the past decades. Through the covalent linkage of electron‐rich and electron‐deficient units, a plethora of medium‐low band gap materials has been developed and tested in organic photovoltaic devices. In particular, the quinoxaline aromatic structure and its derivatives are among the most studied electron deficient aromatic units used in D–A structures. Quinoxaline based materials are endowed with characteristics that are useful for large scale production in real world applications, such as easy synthetic procedures and excellent stability in air. Moreover, the use of quinoxaline based polymers/small molecules in bulk heterojunction (BHJ) devices led to power conversion efficiencies over 9%. Considering the potential of quinoxaline based materials, this review gathers together quinoxaline based polymers and small molecules reported in the literature during the last 5 years, summarizing and discussing the structure‐properties relationships for this class of organic semiconductors, aiming to serve as a background and to promote efforts for the further development of new quinoxaline derivatives with improved and advanced properties for future applications.

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An alternating copolymer of fluorene donor and quinoxaline acceptor versus a terpolymer consisting of fluorene, quinoxaline and benzothiadiazole building units: synthesis and characterization

Cited by 6 publications

References 43 publications

Photoinduced Electron Transfer in Multicomponent Truxene-Quinoxaline Metal–Organic Frameworks

Photoinduced Electron Transfer in Multicomponent Truxene-Quinoxaline Metal–Organic Frameworks

Recent Advances in the Synthesis of Electron Donor Conjugated Terpolymers for Solar Cell Applications

Recent Development of Quinoxaline Based Polymers/Small Molecules for Organic Photovoltaics

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