Synthesis of a new conjugated polymer based on benzimidazole and its sensory properties using the fluorescence‐quenching effect

Choi, Hyun-Woong; Kim, Youn Suk; Yang, Nam Choul; Suh, Dong Hack

doi:10.1002/app.13275

Cited by 9 publications

(3 citation statements)

References 21 publications

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“…Anionic, benzimidazole-containing conjugated polymer 71 was synthesized by Yang et al, and its fluorescence quenching by dimethyl viologen was examined. 117 The polymer was prepared by postpolymerization functionalization with 1,3-propane sultone to install the sulfonatecontaining side chains. In methanol, dimethyl viologen quenched polymer fluorescence with a Stern-Volmer constant of 3.7 × 10 5 .…”

Section: Conjugated Polyelectrolytes and Viologen Quenchersmentioning

confidence: 99%

Chemical Sensors Based on Amplifying Fluorescent Conjugated Polymers

2007

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He spent 1 year as a research chemist at Eastman Kodak, after which he began graduate studies at MIT. He earned his Ph.D. in organic chemistry in 2006, under the supervision of Professor Timothy M. Swager, for studies on luminescent chemosensors. He is currently a postdoctoral fellow in the laboratory of Professor George M. Whitesides at Harvard University. Guy D. Joly obtained his B.A. degree in Chemistry from Hamline University in 1999. He earned his Ph.D. (2004) under the supervision of Professor Eric N. Jacobsen at Harvard University. His Ph.D. research focused on the discovery and development of useful asymmetric catalytic methodologies. After completing his graduate work, he moved to MIT to perform postdoctoral research with Professor Swager in the area of conjugated polymer-based sensors. His research interests broadly encompass organic chemistry, catalysis, sensing, and materials science.(3) Timothy M. Swager is the John D. MacArthur Professor of Chemistry and the Head of the Department of Chemistry at the Massachusetts Institute of Technology. A native of Montana, he received a B.S. from Montana State University in 1983 and a Ph.D. from the California Institute of Technology in 1988. His research interests are in design, synthesis, and study of organic-based electronic, sensory, and liquid crystalline materials.

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Section: Conjugated Polyelectrolytes and Viologen Quenchersmentioning

confidence: 99%

Chemical Sensors Based on Amplifying Fluorescent Conjugated Polymers

2007

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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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“…Imidazoles are an important class of aromatic heterocycles because of their attractive chemical properties, such as acid−base reactions and metal complex forming reactivity . Apart from their importance in biological systems as potential bridging ligands between metal ion centers in metalloenzymes, recent studies have focused on their use as building blocks for extended π-conjugation molecules. − Imidazole is readily converted into cationic imidazolium by the protonation or disubstitution of two N-positions. The 1,3-disubstituted imidazolium ring (Figure a), a cationic N-heteroaromatic ring, is well-known as the most popular and investigated class of the cationic structure of room-temperature ionic liquids. , The reaction of 1,3-disubstituted imidazolium cations is restricted due to the chemical stability of the imidazolium ring derived from the delocalization or burying of cationic charge, the aromaticity, and the low reduction potential.…”

Section: Introductionmentioning

confidence: 99%

Photomodulation of Ionic Interaction and Reactivity: Reversible Photoconversion between Imidazolium and Imidazolinium

et al. 2008

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An interconversion system between imidazolium and imidazolinium has been proposed for the first time. Imidazolium and imidazolinium cations exhibit different reactivity due to the difference in the aromaticity and charge localization structure, which is successfully controlled by means of photoirradiation in the present system. A 4,5-dithiazolylimidazolium salt was prepared and studied as a new class of photochromic materials modulating electrostatic interactions and chemical reactivities. The photochromic 4,5-dithiazolylimidazolium showed reversible photoconversions between imidazolium open-form and imidazolinium closed-form upon successive irradiation with UV and visible light. The imidazolinium closed-form exhibited characteristic solvato- and ionochromisms in which the absorption maximum shifted by more than 80 nm depending on the solvent polarity and counteranions, whereas the imidazolium open-form showed no such solvent-dependent property. Because the corresponding nonionic 4,5-dithiazolylimidazole also did not exhibit the solvent-dependent absorption profile both in open- and closed-forms, the appearance of these chromisms in imidazolinium closed-form was attributed to the change in the extent of ionic interaction, which was brought about by the photoconversion of imidazolium to imidazolinium. The photoderived strong ionic interaction of imidazolinium with counteranion was further applied to the photocontrolled nucleophilic reaction system. Whereas the imidazolium open-form was inert to nucleophiles such as sodium methoxide, the imidazolinium closed-form was reactive to the nucleophilic reaction, demonstrating a photogated reaction system.

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Synthesis of a new conjugated polymer based on benzimidazole and its sensory properties using the fluorescence‐quenching effect

Cited by 9 publications

References 21 publications

Chemical Sensors Based on Amplifying Fluorescent Conjugated Polymers

Chemical Sensors Based on Amplifying Fluorescent Conjugated Polymers

Optical Sensing (Nano)Materials Based on Benzimidazole Derivatives

Photomodulation of Ionic Interaction and Reactivity: Reversible Photoconversion between Imidazolium and Imidazolinium

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