Synthesis, photophysical properties and electroluminescence characterization of 1-phenyl-1H-phenanthro[9,10-d]imidazole derivatives with N-donor substituents

Kula, Sławomir; Ledwon, Przemyslaw; Maroń, Anna; Siwy, Mariola; Grzelak, Justyna; Szalkowski, Marcin; Maćkowski, Sebastian; Schab‐Balcerzak, Ewa

doi:10.1016/j.dyepig.2021.109437

Cited by 10 publications

(12 citation statements)

References 60 publications

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“…In this reaction, the N-H in the structure of imidazole offers variation in derivatization with different substituents. When aniline is added to this condensation reaction, the NH in the structure of imidazole comes into play [19]. Therefore, phenanthroimidazole derivatives are synthesized with the substituent group attached to the hydrogen (N-H) on the nitrogen atom in imidazole.…”

Section: Synthesis Of Phenanthroimidazole Compoundsmentioning

confidence: 99%

“…This method is known by the name Debus–Radziszewski. In this reaction, acetic acid (glacial) is used as the solvent [13, 19]. The ammonium acetate used in the reaction is involved in the formation of imidazole.…”

Section: Imidazole and Phenanthroimidazole Compoundsmentioning

confidence: 99%

“…Phenanthroimidazole compounds consisting of the phenanthrene unit with a high π-conjugation system and imidazole [14,15], with their optical, thermal, and chemical stability and high fluorescence properties, have been the focus of attention of many researchers [16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

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Organic fluorescent compounds based on phenanthroimidazole: A review of highlight studies

et al. 2023

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Organic compounds containing phenanthroimidazole, and its optical, thermal, chemical, and high fluorescence, have drawn the interest of numerous researchers. Phenanthroimidazole derivatives are appealing for various applications due to these characteristics. This research provides a summary of the general information contained in studies on the synthesis, characterization, photophysical characteristics, and possible applications of phenanthroimidazole derivative compounds. The focus of this study revolves around the topic of utilization in technological fields such as sensors, solar cells, optical brighteners, and organic light‐emitting diodes, and covers significant studies on mentioned topics. We anticipate that this study will provide an outline for researchers aiming to further examine fluorescent organic compounds for technological innovations. Furthermore, we anticipate that this research will be crucial in developing long‐term high‐organic compounds for optoelectronic devices.

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Section: Synthesis Of Phenanthroimidazole Compoundsmentioning

confidence: 99%

Section: Imidazole and Phenanthroimidazole Compoundsmentioning

confidence: 99%

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Organic fluorescent compounds based on phenanthroimidazole: A review of highlight studies

et al. 2023

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“…Phenanthroimidazole derivatives exhibit a rigid-planar-conjugate structure and ambipolar characteristics owing to the bonding structures of the two nitrogen atoms of the imidazole ring. , These derivatives have been widely employed as blue light-emitting materials based on their high carrier mobilities and conductivities, high triplet energies, and high fluorescence efficiencies. − Therefore, the phenanthroimidazole unit is a good candidate for the fabrication of COFs. However, no well-defined COF synthetic route from phenanthroimidazole derivatives has been reported to date.…”

Section: Introductionmentioning

confidence: 99%

Phenanthroimidazole-Based Covalent Organic Frameworks with Enhanced Activity for the Photocatalytic Hydrogen Evolution Reaction

Liu

Pan

Seo

et al. 2023

ACS Appl. Energy Mater.

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The rational design of organic semiconductors based on crystalline covalent organic frameworks (COFs) as efficient photocatalysts is highly desirable. In this study, the first example of phenanthroimidazole-based COFs is reported: PIm-COF1 with an imine linkage and PIm-COF2 with a β-ketoenamine-linkage. Both COF materials showed substantial optical properties. The average hydrogen evolution rate was 7417.5 μmolg −1 h −1 for PIm-COF2, which was 14 times higher than that of PIm-COF1 (528.5 μmolg −1 h −1 ). This can be attributed to the strong donor− acceptor effect of PIm-COF2 and the continuous separation and transfer of the photoexcited electron−hole pair from the phenanthro[9,10-d] imidazole moiety which are verified by timedependent density functional theory and excitation state analysis.

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“…Currently, organic compounds known as small molecules (SMs) have been increasingly studied in this role [16][17][18][19][20][21][22][23][24]30,31]. An example of compounds of this type are the very popular phenanthroimidazole derivatives [17][18][19][20][22][23][24]30,31,[34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50]. Their decisive advantage is simple and cheap synthesis.…”

Section: Introductionmentioning

confidence: 99%

Progress on Phenanthroimidazole Derivatives for Light-Emitting Electrochemical Cells: An Overview

Szłapa-Kula

Kula

2023

Energies

Self Cite

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Phenanthroimidazole derivatives are currently frequently used chemical compounds in the active layers of various devices, such as organic light-emitting diodes (OLEDs) or light-emitting electrochemical cells (LECs). Their advantages include simple and cheap synthesis, good solubility in organic solvents, easy processing, high thermal stability, excellent electron transport ability, and very good optical and electroluminescent properties. The construction of the LEC is based on a very simple construction in which the active layer plays a significant role. Thus, the compounds used in it are extremely important because they play the role of more than just emitters. This review summarizes the current state of the art regarding phenanthroimidazole derivatives used in the active layer in LECs. The synthesis of the considered compounds is presented in detail in the first part of the review. Next, research on the physicochemical properties of phenanthroimidazole derivatives is presented. Finally, the latest reports on LEC test devices are presented.

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Synthesis, photophysical properties and electroluminescence characterization of 1-phenyl-1H-phenanthro[9,10-d]imidazole derivatives with N-donor substituents

Cited by 10 publications

References 60 publications

Organic fluorescent compounds based on phenanthroimidazole: A review of highlight studies

Organic fluorescent compounds based on phenanthroimidazole: A review of highlight studies

Phenanthroimidazole-Based Covalent Organic Frameworks with Enhanced Activity for the Photocatalytic Hydrogen Evolution Reaction

Progress on Phenanthroimidazole Derivatives for Light-Emitting Electrochemical Cells: An Overview

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