Synthesis and Optoelectronic Properties of Hexa‐<i>peri</i>‐hexabenzoborazinocoronene

Dosso, Jacopo; Tasseroul, Jonathan; Fasano, Francesco; Marinelli, Davide; Biot, Nicolas; Fermi, Andrea; Bonifazi, Davide

doi:10.1002/ange.201700907

Cited by 25 publications

(19 citation statements)

References 51 publications

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“…The synthesis and photophysical characterization of 1 in solution was reported elsewhere, 32 showing blue-green fluorescence and yellow-orange phosphorescence at room temperature and 77 K, respectively -Figure S2. We have further prepared thin-films with only 1 and with blends of 1 with the polymer electrolyte mixture used in devicesi.e., 1:PS:PEO:LiOTf in a mass ratio 10:0.9:2.6:0.78, being PS (polystyrene), PEO (polyethylene oxide), and LiOTf (Lithium Triflate); see Supporting Information (SI) for more details.…”

Section: Resultsmentioning

confidence: 99%

“…Along these lines, the major thrust of this work is the unveiling of the impact of the selfheating on the chromaticity and efficiency of LECs using a benchmark nanographenei.e., hexaperihexabenzocoronene or 1 32 as an emerging class of emitters with outstanding device performance. Since LECs show a high versatility with respect to the type of emitters, 4,23,[33][34][35][36][37][38][39] the impact of self-heating can, indeed, be considered as universal.…”

Section: Introductionmentioning

confidence: 99%

“…25 Our interest on nanographenes lies on their high ϕ, ambipolar carrier properties, sound thermal and redox stabilities, and a good solubility in common organic solvents. 32,41,42 Despite these appealing properties, they have barely been investigated as emitters in thin-film lighting devices. 41 In stark contrast, we have recently reported highly stable and efficient red-emitting LECs with contorted nanographenes 24 and highly efficient white-emitting LECs with B-N doped nanographenesvide supra.…”

Section: Introductionmentioning

confidence: 99%

“…synthesized as reported in a previous contribution 32. Absorption spectra were recorded with a Perkin Elmer Lambda 35 UV-Vis spectrometer.…”

mentioning

confidence: 99%

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Revealing the Impact of Heat Generation Using Nanographene-Based Light-Emitting Electrochemical Cells

Fresta

Dosso

Cabanillas‐González

et al. 2020

ACS Appl. Mater. Interfaces

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Self-heating in light-emitting electrochemical cells (LECs) has been long overlooked, while it has a significant impact on i) device chromaticity by changing the electroluminescent band shape, ii) device efficiency due to thermal quenching and exciton dissociation reducing the external quantum efficiency (EQE), and iii) device stability due to thermal quenching of excitons and formation of doped species, phase separation, and collapse of the intrinsic emitting zone. Herein, we reveal, for the first time, a direct relationship between self-heating and the early changes of the device chromaticity as well as the magnitude of the error comparing theoretical/experimental EQEs -i.e., overestimation error of ca. 35 % at usual pixel working temperatures of around 50 °C. This has been realized in LECs using a benchmark nanographene i.e., a substituted hexa-peri-hexabenzocoronene -as an emerging class of emitters with outstanding device performance compared to the prior-art of small molecule LECs -e.g., luminances of 345 cd/m 2 and EQEs of 0.35%. As such, this work is a fundamental contribution highlighting how self-heating is a critical limitation towards the optimization and wide use of LECs.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…synthesized as reported in a previous contribution 32. Absorption spectra were recorded with a Perkin Elmer Lambda 35 UV-Vis spectrometer.…”

mentioning

confidence: 99%

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Revealing the Impact of Heat Generation Using Nanographene-Based Light-Emitting Electrochemical Cells

Fresta

Dosso

Cabanillas‐González

et al. 2020

ACS Appl. Mater. Interfaces

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“…While attempting different synthetic strategies to prepare hexabenzo-borazinocoronene, 26 we prepared the NBN-doped isostere of a benzo[fg]tetracenyl anion ( Figure 1). Derivatives of the NBN-doped isostere were firstly prepared independently by the groups of Hatekeyama 27 and Feng 28 .…”

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confidence: 99%

Probing Peripheral H-Bonding Functionalities in BN-Doped Polycyclic Aromatic Hydrocarbons

et al. 2020

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The replacement of carbon atoms at the zigzag periphery of a benzo[fg]tetracenyl derivative with an NBN atomic triad allows the formation of heteroatom-doped PAHs isosteres, which expose BN mimics of the amidic NH functions. Their ability to form H-bonded complexes has never been touched so far. Herein we report the first solution recognition studies of peripherally NBN-doped PAHs to form doubly H-bonded DD•AA and ADDA•DAAD-type complexes with suitable complementary H-bonding acceptor partners. The first determination of the Ka in solution showed that the 1:1 association strength is around 27 ± 1 M-1 for the DD•AA complexes in C6D6, whereas it rises to 1820 ± 130 M-1 for the ADDA•DAAD array in CDCl3. Given the interest of BNdoped polyaromatic hydrocarbons in supramolecular and materials chemistry, it is expected that these findings will open new possibilities to design novel materials, where the H-bonding properties of peripheral NH hydrogens could serve as anchors to tailor the organizational properties of PAHs. INTRODUCTION Following the vigorous synthetic developments of polycyclic aromatic hydrocarbons (PAHs), 1 the substitution (i.e., doping) of sp 2-carbon atoms with isoelectronic and isostructural BN couples is re-emerging as a versatile approach to tune the optoelectronic properties of these materials. 2-7 In particular, borazines 8,9 and BN-doped PAHs (e.g., azaborines, 10,11 borazapyrenes, 12,13 borazaphenanthrenes 12,14 borazanaphthalenes, 15,16 borazaanthracene 17,18 and boraazaperylene 19) are now increasingly attracting the attention of the physical and chemical community for their use in a broad spectrum of optoelectronic applications. 20-22 When used to decorate a periphery, nonsubstituted BN couples terminate with NH functions that, being more acidic than the CH analogues, could engage into H-bonding interactions as observed with boronic acids. 23 For instance, Liu and co-workers showed in a seminal report that 1,2-dihydro-1,2-azaborine can act as an H-bonding donor in the solid state and engage into a H-bond with the C=O

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Synthesis and Applications of Organic Borazine Materials

Marchionni,

Basak,

Khodadadi

et al. 2023

Adv Funct Materials

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The past decade has marked a renewed interest in borazines and BN‐doped polycyclic aromatic hydrocarbons. This is predominantly because of new advances that have highlighted their potential in various applications, including gas separation and storage, organic (opto)electronics, catalysis, and as supramolecular systems. This review gives a critical overview of the most significant approaches to the synthesis of (substituted) B3N3 motifs and focuses on the discussion of those borazine‐doped carbon structures that have been developed for potential use in materials science applications.

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Synthesis and Optoelectronic Properties of Hexa‐peri‐hexabenzoborazinocoronene

Cited by 25 publications

References 51 publications

Revealing the Impact of Heat Generation Using Nanographene-Based Light-Emitting Electrochemical Cells

Revealing the Impact of Heat Generation Using Nanographene-Based Light-Emitting Electrochemical Cells

Probing Peripheral H-Bonding Functionalities in BN-Doped Polycyclic Aromatic Hydrocarbons

Synthesis and Applications of Organic Borazine Materials

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