Synthesis and photophysical properties of 1,2‐diphenylindolizine derivatives: fluorescent blue‐emitting materials for organic light‐emitting device

Song, Yeong Ran; Lim, Choon Woo; Kim, Tae Woo

doi:10.1002/bio.2968

Cited by 38 publications

(9 citation statements)

References 53 publications

(75 reference statements)

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“…The HOMO and LUMO energy levels and the corresponding energy gap have been mentioned in the Table . The LUMO energy levels were calculated using the formula E LUMO =‐(4.8 ‐E 1/2,Fc,Fc + + E red,onset ) eV, whereas the HOMO energy levels were measured using the formula E HOMO =‐(4.8 ‐ E 1/2,Fc,Fc + + E oxd,onset ) eV . A comparison of band gaps via UV‐vis, CV and DFT studies is given in Table .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Mesomorphism and Photoluminescence of a New Class of Anthracene-based Discotic Liquid Crystals

Setia

Pal

2016

ChemistrySelect

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Four discotic liquid crystals (DLCs) based on anthracene, a novel redox active central core, have been synthesized and their mesomorphic behavior investigated. Among them, two of the derivatives showed stable hexagonal plastic mesophases whereas other two exhibited a columnar nematic phase at near room temperature as derived by X-ray scattering results. Type of the mesophases formed by these new class of compounds are rare that renders the central anthracene core attractive in the search for new functional DLC materials. HOMO-LUMO val-ues have also been found to be much less in these materials which make them as good candidates for electron migration studies in self-organized systems. All the compounds show blue luminescence in solution under the long wavelength UV light. Overall, these new class of materials are promising, considering the emissive nature, ease of synthesis and stabilization of unconventional mesophases at room temperature or near room temperature.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Mesomorphism and Photoluminescence of a New Class of Anthracene-based Discotic Liquid Crystals

Setia

Pal

2016

ChemistrySelect

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“…Indolizines, a class of heteroaromatic compounds containing two condensed rings (5‐ and 6‐membered) and a bridging nitrogen atom, have been widely applied in natural products and synthetic pharmaceuticals, These types of compounds have also been applied as dyes and biological markers due to their photophysical properties . Therefore, the development of efficient methods for the synthesis of indolizines continues to attract the attention of organic chemists.…”

Section: Methodsmentioning

confidence: 99%

Hemoglobin‐Catalyzed Synthesis of Indolizines Under Mild Conditions

Tang

et al. 2019

Eur J Org Chem

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Hemoglobin-catalyzed synthesis of indolizines via a multicomponent reaction has been reported for the first time. The corresponding indolizines were obtained in moderate to high yields by using this method. This mild, efficient and practical method is distinguished by the use of a commercially inex-Indolizines, a class of heteroaromatic compounds containing two condensed rings (5-and 6-membered) and a bridging nitrogen atom, have been widely applied in natural products and synthetic pharmaceuticals. [1,2] These types of compounds have also been applied as dyes and biological markers due to their photophysical properties. [3][4][5][6][7] Therefore, the development of efficient methods for the synthesis of indolizines continues to attract the attention of organic chemists. Traditional synthetic routes to indolizines mainly comprise the Scholtz or Chichibabin reactions. More recently, cycloaddition reactions (1,3-dipolar cycloadditions), intramolecular cyclizations using acetic anhydride, formation of C3-C4 bond, formation of C1-C9 bond, and formation of C8-C9 bond have been reported. [8][9][10][11][12][13][14] However, most of these methods suffer from some drawbacks, such as the formation of conjugate-acid waste, narrow substrate scope, harsh reaction conditions, need for toxic transition-metal catalysts and harmful organic solvents. Thus, an environmentally preferable and efficient method to synthesize indolizines for practical applications must be developed.Biocatalysis is a highly attractive strategy in organic synthesis for organic synthesis due to its efficient, selective and environment-friendly characteristics. [15] A new biocatalytic approach relies on the promiscuity of enzymes to catalyze reactions that are different than their native functions. This interesting property of protein allows chemists to explore new types of biocatalytic organic reactions and dramatically expands the application of catalytic proteins within the field of organic chemistry. [16][17][18][19][20][21][22] [a]

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“…When 1,3-dipolar cycloaddition of pyridinium ylides with electron-deficient olefins or alkynes is followed by oxidative aromatization (spontaneous or chemically induced) a convergent and straightforward access toward functionalized indolizines is arranged. Many excellent examples of this synthetic sequence (cycloaddition/aromatization) have been published (for examples see [75,[77][78][79][80][81][82]) as indolizine is an important skeletal structure present in many natural and synthetic bioactive molecules (for examples see [83][84][85][86][87][88][89][90][91][92][93]) and in material with photochemical properties [94][95][96][97][98][99][100][101][102]. Pivina and co-authors recently reported quantum chemical calculations on the spatial and electronic structure of pyridinium ylides, as well as the modelling of their1,3-dipolar cycloadddition reactions.…”

Section: Pyridinium Ylidesmentioning

confidence: 99%

Nucleophilic Dearomatization of Activated Pyridines

2018

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Amongst nitrogen heterocycles of different ring sizes and oxidation statuses, dihydropyridines (DHP) occupy a prominent role due to their synthetic versatility and occurrence in medicinally relevant compounds. One of the most straightforward synthetic approaches to polysubstituted DHP derivatives is provided by nucleophilic dearomatization of readily assembled pyridines. In this article, we collect and summarize nucleophilic dearomatization reactions of - pyridines reported in the literature between 2010 and mid-2018, complementing and updating previous reviews published in the early 2010s dedicated to various aspects of pyridine chemistry. Since functionalization of the pyridine nitrogen, rendering a (transient) pyridinium ion, is usually required to render the pyridine nucleus sufficiently electrophilic to suffer the attack of a nucleophile, the material is organized according to the type of N-functionalization. A variety of nucleophilic species (organometallic reagents, enolates, heteroaromatics, umpoled aldehydes) can be productively engaged in pyridine dearomatization reactions, including catalytic asymmetric implementations, providing useful and efficient synthetic platforms to (enantioenriched) DHPs. Conversely, pyridine nitrogen functionalization can also lead to pyridinium ylides. These dipolar species can undergo a variety of dipolar cycloaddition reactions with electron-poor dipolarophiles, affording polycyclic frameworks and embedding a DHP moiety in their structures.

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Synthesis and photophysical properties of 1,2‐diphenylindolizine derivatives: fluorescent blue‐emitting materials for organic light‐emitting device

Cited by 38 publications

References 53 publications

Synthesis, Mesomorphism and Photoluminescence of a New Class of Anthracene-based Discotic Liquid Crystals

Synthesis, Mesomorphism and Photoluminescence of a New Class of Anthracene-based Discotic Liquid Crystals

Hemoglobin‐Catalyzed Synthesis of Indolizines Under Mild Conditions

Nucleophilic Dearomatization of Activated Pyridines

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