Indoloquinoxaline as a terminal building block for the construction of π-conjugated small molecules relevant to organic electronics

Payne, Abby‐Jo; McCahill, Jenny S. J.; Welch, Gregory C.

doi:10.1016/j.dyepig.2015.07.035

Cited by 19 publications

(12 citation statements)

References 58 publications

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“…This heterogeneous alternative proved to be equally or more active than the common homogeneous catalysts Pd(PPh 3 ) 4 , Pd(PPh 3 ) 2 Cl 2 and Pd(OAc) 2 offering advantages in terms of activity, selectivity, stability and trace metal contamination. Integrating the use of this heterogeneous catalyst whenever possible, we have established a large variety of materials that can be synthesized using this catalyst system. − …”

Section: Introductionmentioning

confidence: 99%

“…We are interested in the incorporation of organic dyes as the core component of our molecular framework. Previous work by our research group, and others have focused on the design and synthesis of π-conjugated dye-based materials incorporating isoindigo − ,,− and diketopyrrolopyrrole ,,,,, building blocks for use in solar cell devices. Although these materials do offer the inherent strong absorptive properties of typical organic dyes, their onsets of absorption do not often reach 700 nm.…”

Section: Introductionmentioning

confidence: 99%

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The Optimization of Direct Heteroarylation and Sonogashira Cross-Coupling Reactions as Efficient and Sustainable Synthetic Methods To Access π-Conjugated Materials with Near-Infrared Absorption

McAfee

Cann

Josse

et al. 2016

ACS Sustainable Chem. Eng.

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Two π-conjugated thienoisoindigo-based organic small molecules have been designed to be synthetically accessible through sustainable direct heteroarylation or Sonogashira C–C bond forming cross-coupling reactions utilizing a heterogeneous palladium catalyst. To access these materials, one molecule, TII-ThNaph2, contains a thiophene π-bridge to facilitate direct heteroarylation protocols, whereas the other, TII-AcNaph2, contains an acetylene π-bridge required for Sonogashira couplings. The synthetic route to both final materials was optimized to investigate the reactivity of thienoisoindigo, which to this point has not been significantly explored in comparison to other popular organic dyes such as diketopyrrolopyrrole and isoindigo. Considering the reported interest of thienoisoindigo-based materials in organic solar cells and field-effect transistors, both final materials have been characterized for their optical, electrochemical and thermal properties offering a comparison of the structure–property relationships that manifest as a result of the two different π-bridging units.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The Optimization of Direct Heteroarylation and Sonogashira Cross-Coupling Reactions as Efficient and Sustainable Synthetic Methods To Access π-Conjugated Materials with Near-Infrared Absorption

McAfee

Cann

Josse

et al. 2016

ACS Sustainable Chem. Eng.

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“…The development and design of small π-conjugated molecules have attracted increasing attention for their inspiring applications in the fields of solar cells [1][2][3], organic devices [4][5][6][7][8], and as chemosensors [9,10]. The acridine core (Figure 1), formed by two benzenes fused to a pyridine ring, is among the most exten-sively studied heterocyclic aromatic compounds.…”

Section: Introductionmentioning

confidence: 99%

2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

Tka¹,

Ayed²,

Braiek³

et al. 2021

Beilstein J. Org. Chem.

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Acridine derivatives have attracted considerable interest in numerous areas owing to their attractive physical and chemical properties. Herein, starting from readily available anthranilic acid, an efficient synthesis of 2,4-bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridine derivatives was accomplished via a one-pot double Sonogashira cross-coupling method. The UV-visible absorption and emission properties of the synthesized molecules have been examined. Additionally, theoretical studies based on density functional theory (DFT/B3LYP/6-31G(d)) were carried out.

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“…π-Conjugated organic molecules are finding use in numerous areas ranging from organic electronics [1][2][3][4][5], ions sensing [6,7], and solar cell development [8][9][10]. Within this background, acridines represent an interesting class of heteroaromatic π-conjugated compounds [11][12][13][14] which show great perspectives in medicinal chemistry [15][16][17][18][19][20][21][22][23], dye industries [24][25][26], and metal chemo sensing [27][28][29].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and investigation on optical and electrochemical properties of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridines

Tka¹,

Ayed²,

Braiek³

et al. 2021

Beilstein J. Org. Chem.

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A facile synthesis of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridine derivatives is reported which is based on POCl3-mediated cyclodehydration followed by double Suzuki–Miyaura cross-coupling. The absorption and fluorescence properties of the obtained products were investigated and their HOMO/LUMO energy levels were estimated by cyclic voltammetry measurements. Besides, density functional theory calculations were carried out for further exploration of their electronic properties.

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Indoloquinoxaline as a terminal building block for the construction of π-conjugated small molecules relevant to organic electronics

Cited by 19 publications

References 58 publications

The Optimization of Direct Heteroarylation and Sonogashira Cross-Coupling Reactions as Efficient and Sustainable Synthetic Methods To Access π-Conjugated Materials with Near-Infrared Absorption

The Optimization of Direct Heteroarylation and Sonogashira Cross-Coupling Reactions as Efficient and Sustainable Synthetic Methods To Access π-Conjugated Materials with Near-Infrared Absorption

2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

Synthesis and investigation on optical and electrochemical properties of 2,4-diaryl-9-chloro-5,6,7,8-tetrahydroacridines

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