Synthesis and Optoelectronic Properties of 6,12-Bis(amino)anthanthrene Derivatives

Giguère, Jean-Benoît; Morin, Jean‐François

doi:10.1021/jo402313c

Cited by 25 publications

(25 citation statements)

References 30 publications

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“…In these cases the target azaacene core was first obtained in one step and then functionalized with solubilizing side groups such as triisopropylsilylethynyl by forming a −C≡C− linkage with the core in a second step . Compounds in which other groups link the solubilizing side chain with the core, such as −CH 2 NH− and −CH=N−, were also synthesized . Recently, bis‐tetracene diketone, first reported in 1949, to which two triisopropylsilylethynyl groups were attached, was used as a substrate in the synthesis of several acenes, and gave good solubility of the functionalized semiconductors in organic solvents …”

Section: Introductionmentioning

confidence: 99%

Soluble Flavanthrone Derivatives: Synthesis, Characterization, and Application to Organic Light‐Emitting Diodes

Kotwica

Bujak

Data

et al. 2016

Chemistry A European J

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Simple modification of benzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridine-8,16-dione, an old and almost-forgotten vat dye, by reduction of its carbonyl groups and subsequent O-alkylation, yields solution-processable, electroactive, conjugated compounds of the periazaacene type, suitable for the use in organic electronics. Their electrochemically determined ionization potential and electron affinity of about 5.2 and -3.2 eV, respectively, are essentially independent of the length of the alkoxyl substituent and in good agreement with DFT calculations. The crystal structure of 8,16-dioctyloxybenzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridine (FC-8), the most promising compound, was solved. It crystallizes in space group P1‾ and forms π-stacked columns held together in the 3D structure by dispersion forces, mainly between interdigitated alkyl chains. Molecules of FC-8 have a strong tendency to self-organize in monolayers deposited on a highly oriented pyrolytic graphite surface, as observed by STM. 8,16-Dialkoxybenzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridines are highly luminescent, and all have photoluminescence quantum yields of about 80 %. They show efficient electroluminescence, and can be used as guest molecules with a 4,4'-bis(N-carbazolyl)-1,1'-biphenyl host in guest/host-type organic light-emitting diodes. The best fabricated diodes showed a luminance of about 1900 cd m(-12) , a luminance efficiency of about 3 cd A(-1) , and external quantum efficiencies exceeding 0.9 %.

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Section: Introductionmentioning

confidence: 99%

Soluble Flavanthrone Derivatives: Synthesis, Characterization, and Application to Organic Light‐Emitting Diodes

Kotwica

Bujak

Data

et al. 2016

Chemistry A European J

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“…[18] While searching for new biradical molecules, we used the anthanthrone core as as tartingp oint. [21] Then, aC asto-Stephen-Sonogashira coupling using triisopropylsilylacetylene (TIPSA) with compound 1 or compound 2 in toluenea fforded compounds 3 and 4 respectively,b oth in 99 %y ield. [19] It has been previouslyd emonstrated that anthanthronec an form as table biradical in an excited state by mechanochemistry on the solid sample (Figure 1, top).…”

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confidence: 99%

Wurster‐Type Nanographenes as Stable Diradical Dications

Desroches

Morin

2018

Chemistry A European J

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Three new and stable diradical dications based on the 4,10-dibromoanthanthrone have been synthesized and characterized. In their dicationic state, the amines show a biradical character in the ground state. Their magnetic properties have been investigated by NMR and EPR spectroscopies. The dicationic salts shows strong and broad optical absorption in the near-infrared region. The main driving force to obtain a ground state biradical is the high steric hindrance that prevents planarization of the diphenylamines with the anthanthrone aromatic core. The radical cations are isolated in two perpendicular π-systems as demonstrated by X-ray diffraction structures. This work provides a new bridging unit in the search for biradical bis(triarylamines) salts.

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“…Thus, the extension of conjugation through these positions has only a slight effect on the band gap (high dihedral angle) . We have shown that the dihedral angle between anthanthrene and other π‐conjugated units can be reduced by forming intramolecular H‐bonding, but this strategy required the presence of an heteroatom directly attached to the anthanthrene, which limits the choice of functional groups that can be used to modulate the electronic properties …”

Section: Zigzag‐edged Pahs For Oscsmentioning

confidence: 99%

Polycyclic Aromatic Hydrocarbons as Potential Building Blocks for Organic Solar Cells

Aumaître

Morin

2019

The Chemical Record

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Since the discovery of graphene in the early 2000′s, polycyclic aromatic hydrocarbons (PAHs) have been resurrected and new synthetic tools have been developed to prepare unprecedented structures with unique properties. One application that has been overlooked for this class of molecules is organic solar cells (OSCs). In this account, we present the recent development in the preparation of moderate to low band gap PAHs that could potentially be used as semiconducting materials in OSCs. Our focus is directed toward all‐carbon PAHs as well as their polymeric analogs.

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Synthesis and Optoelectronic Properties of 6,12-Bis(amino)anthanthrene Derivatives

Cited by 25 publications

References 30 publications

Soluble Flavanthrone Derivatives: Synthesis, Characterization, and Application to Organic Light‐Emitting Diodes

Soluble Flavanthrone Derivatives: Synthesis, Characterization, and Application to Organic Light‐Emitting Diodes

Wurster‐Type Nanographenes as Stable Diradical Dications

Polycyclic Aromatic Hydrocarbons as Potential Building Blocks for Organic Solar Cells

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