Multifunctional copolyfluorene containing pendant benzimidazolyl groups: applications in chemical sensors and electroluminescent devices

Wu, Chia Shing; Liu, Chao Te; Chen, Yun

doi:10.1039/c2py20506h

Cited by 19 publications

(8 citation statements)

References 54 publications

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“…Aiming to facilitate such analysis, Figure illustrates the alignment of the frontier levels of the evaluated polymers in relation to the HOMO and LUMO of typical acceptor compounds, as well as the work functions of electrodes commonly employed (or at least proposed) in flexible devices . In order to allow direct comparisons, our theoretical results for the HOMO values of the free MEH‐PPV and P3HT models were shifted to match the experimental HOMO values typically found in polymeric solutions of MEH‐PPV and P3HT …”

Section: Resultsmentioning

confidence: 99%

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Effects of Mechanical Stretching on the Properties of Conjugated Polymers: Case Study for MEH‐PPV and P3HT Oligomers

Roldao

Batagin‐Neto

Lavarda

et al. 2018

J Polym Sci B Polym Phys

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Nowadays, the development of new materials for applications in flexible optoelectronic devices is one of the main frontiers of science. However, in order to improve the applicability and durability of such devices, a deeper understanding of the effects induced by mechanical deformations on the properties of their components is still necessary. In this sense, in the present study, it is evaluated the effect of mechanical stretching in the structural, electronic, and optical responses of two widely investigated organic polymers with great technological interest: poly(2-methoxy,5-(2 0ethylhexyloxy)-1,4-phenylene vinylene) and poly(3-hexylthiophene-2,5-diyl). Hartree-Fock and density functional theory electronic structure calculation methods were employed for the study of oligomeric structures subjected to increasing stretch levels along the polymerization axis. The results show a dependence of the polymer properties with the mechanical deformation, allowing to identify distinct response regimes according to the main chain stretching. In particular, it is noticed that large stretches lead to nonfunctional devices, mainly due to the localization of the frontier orbitals and degradation of optoelectronic properties. In addition, it was also identified that very small deformations can lead to some interesting optoelectronic responses, which could indicate an alternative route for the design of organic devices via mechanical processes.

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Section: Resultsmentioning

confidence: 99%

“…Alignments between the frontier energy levels of the polymers and the frontier levels/work functions of typical acceptors and electrodes employed in flexible organic devices . [Color figure can be viewed at wieyonlinelibrary.com] …”

Section: Resultsmentioning

confidence: 99%

Effects of Mechanical Stretching on the Properties of Conjugated Polymers: Case Study for MEH‐PPV and P3HT Oligomers

Roldao

Batagin‐Neto

Lavarda

et al. 2018

J Polym Sci B Polym Phys

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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%

“…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. For example, a copolymer built from N-(1-ethyl-2-(pyridin-4-yl)-1Hbenzo[d]imidazol-5-yl)methacrylamide and 2-hydroxyethyl methacrylate exhibits a pH sensitivity due to acid-base equilibria on the heteroatom of pyridyl-substituted benzimidazole moiety [30] (Figure 2A).…”

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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“…New and more efficient luminescent materials with potential application in devices, solar cells and sensors have been suggested for the last two decades. Particularly those employing poly(phenylenevinylene) derivatives have attracted the attention of science and technology [1,2]. Common strategies are to combine compounds with distinct photophysical properties in multi-layers, blends, doped films and membranes, in order to obtain the most efficient active layer for these devices, but aiming to distinct micromorphologies, leading to high ordered materials to minimize intragap electronic states related to defects [3], blends presenting long-lived exciton characteristics by limiting the recombination of polarons in their heterojunction [4], charge-transfer complexes formation that are taken as entities that can modulate the performance of organic solar cells by influencing the morphology of donor-acceptor blends [5] and even by influencing chain aggregation, which results in more efficient energy transfer processes due to effective interfacial interactions, at least when one of the compounds is in low content [6].…”

Section: Introductionmentioning

confidence: 99%

Relaxation Processes and Polymeric Chain Interpenetration in a PMMA-Cz/ MEH-PPV Blend Studied by Fluorescence Spectroscopy

Martins¹,

Atvars²

2013

J. Compos. Biodegradable Polym.

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Miscibility and energy transfer processes of a blend containing 0.1 % of Poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene] (MEH-PPV) in a matrix of poly(methyl-methacrylate) containing 1% of attached carbazolyl groups (PMMA-Cz) were studied by fluorescence spectroscopy and microscopy techniques. From SEM micrographs, a uniform surface is found. The images on the cryogenic fracture of the blend does not show domains, although from fluorescence optical microscopy domains of MEH-PPV of about 30 μm in the PMMA-Cz matrix were observed, indicating the immiscibility of the blend components. By steady-state and time-resolved fluorescence spectroscopies measured at room temperature and at 77 K, it was found that there is an important non-radiative energy transfer occurring by Forster mechanism and due to that, there must be an interpenetration degree between polymeric chains specially at room temperature, which is evidence for miscibility. This can be inferred also by temperature-dependent fluorescence spectroscopy, which informs about relaxation processes occurring in the blend and also reveals the occurrence of an interface effect that is characteristic of miscible components.

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Multifunctional copolyfluorene containing pendant benzimidazolyl groups: applications in chemical sensors and electroluminescent devices

Cited by 19 publications

References 54 publications

Effects of Mechanical Stretching on the Properties of Conjugated Polymers: Case Study for MEH‐PPV and P3HT Oligomers

Effects of Mechanical Stretching on the Properties of Conjugated Polymers: Case Study for MEH‐PPV and P3HT Oligomers

Optical Sensing (Nano)Materials Based on Benzimidazole Derivatives

Relaxation Processes and Polymeric Chain Interpenetration in a PMMA-Cz/ MEH-PPV Blend Studied by Fluorescence Spectroscopy

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