Homoconjugation effects in triptycene based organic optoelectronic materials

Mistry, Jai-Ram; Montanaro, Stephanie; Wright, Iain A.

doi:10.1039/d2ma00523a

Cited by 19 publications

(15 citation statements)

References 106 publications

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“…0.31 V ( E HOMO =−5.11 eV) (Figure S5). This finding indicates a slightly stronger electron‐donating effect of the Tp moiety than the t ‐Bu group, presumably due to the homoconjugation effects of the benzene rings in triptycene [14d] . Next, we investigated the photophysical characteristics of 2 wt % Tp‐DABNA and t ‐DABNA doped films in a mixed host matrix composed of 3,3′‐di‐(9 H ‐carbazol‐9‐yl)‐1,1′‐biphenyl (mCBP, 50 wt %) and bis[2‐(diphenylphosphino)phenyl]ether oxide (DPEPO, 50 wt %).…”

Section: Resultsmentioning

confidence: 95%

Triptycene‐Fused Sterically Shielded Multi‐Resonance TADF Emitter Enables High‐Efficiency Deep Blue OLEDs with Reduced Dexter Energy Transfer

et al. 2023

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Designing multi-resonance (MR) emitters that can simultaneously achieve narrowband emission and suppressed intermolecular interactions is challenging for realizing high color purity and stable blue organic lightemitting diodes (OLEDs). Herein, a sterically shielded yet extremely rigid emitter based on a triptycene-fused B,N core (Tp-DABNA) is proposed to address the issue. Tp-DABNA exhibits intense deep blue emissions with a narrow full width at half maximum (FWHM) and a high horizontal transition dipole ratio, superior to the wellknown bulky emitter, t-DABNA. The rigid MR skeleton of Tp-DABNA suppresses structural relaxation in the excited state, with reduced contributions from the medium-and high-frequency vibrational modes to spectral broadening. The hyperfluorescence (HF) film composed of a sensitizer and Tp-DABNA shows reduced Dexter energy transfer compared to those of t-DABNA and DABNA-1. Notably, deep blue TADF-OLEDs with the Tp-DABNA emitter display higher external quantum efficiencies (EQE max = 24.8 %) and narrower FWHMs (� 26 nm) than t-DABNA-based OLEDs (EQE max = 19.8 %). The HF-OLEDs based on the Tp-DABNA emitter further demonstrate improved performance with an EQE max of 28.7 % and mitigated efficiency roll-offs.

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Section: Resultsmentioning

confidence: 95%

Triptycene‐Fused Sterically Shielded Multi‐Resonance TADF Emitter Enables High‐Efficiency Deep Blue OLEDs with Reduced Dexter Energy Transfer

et al. 2023

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“…This is possibly due to homoconjugation occurring through the sp 3 -hybridized carbon, given the similarity in the HOMO energy levels between the t Cz units and the DICz core (Figure S2). − However, the natural transition orbitals (highest occupied natural transition orbital (HONTO) and lowest unoccupied natural transition orbital (LUNTO)) of 4 t Cz-DICz indicate that the DICz cores are mainly responsible for the electronic transitions, even though the HOMO of 4 t Cz-DICz is found to be extended to the t Cz units (Figure c).…”

Section: Resultsmentioning

confidence: 99%

Novel π-Extended Indolocarbazole-Based Deep-Blue Fluorescent Emitter with Remarkably Narrow Bandwidth for Solution-Processed Organic Light-Emitting Diodes

Jung,

Park,

Kwon

et al. 2023

ACS Appl. Mater. Interfaces

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“…11−15 This strategy has been evaluated and explored for potential applications in organic optoelectronics, such as light-emitting devices (OLEDs), organic solar cells (OSCs), and charge transport/ storage technologies. 13 In addition, shape-persistent triptycenerelated synthons have been widely used in porous materials, such as metal−organic and covalent−organic frameworks (MOFs and COFs, respectively) and organic cages, with applications in areas such as catalysis, pollutant removal, and gas storage. 16−22 Benzimidazoles have important roles in several fields.…”

Section: Introductionmentioning

confidence: 99%

Homoconjugation and Tautomeric Isomerism in Triptycene-Fused Pyridylbenzimidazoles

Preda,

Mobili,

Ravelli

et al. 2024

J. Org. Chem.

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The facile, metal-free synthesis and characterization of three new series of triptycene-fused pyridylbenzimidazoles are reported; such compounds possess an imidazole moiety fused within the benzene rings of the trypticene and a pyridine ring installed at position 2 of the imidazole rings. The position of the nitrogen atom of the pyridyl moiety linked to position 2 of the fused benzimidazole scaffold is systematically changed from the ortho to para position. The number of substituted blades bearing the pyridyl-substituted fused benzimidazole scaffolds has been increased from one to three. Such a library of compounds allowed us to evaluate the enhancement of two main effects: tautomeric isomerism and homoconjugation. The characteristic dynamic equilibrium between different isomers induced by prototropic tautomerization was examined by 1H nuclear magnetic resonance spectroscopy. By comparison of the photophysical properties of the new compounds with those of classical planar pyridylbenzimidazoles, the presence of the homoconjugation effect between the different triptycene blades was demonstrated. Fine details of the electronic structure of the new derivatives were unraveled by a computational analysis. The novel compounds can be employed for the construction of intriguing self-assembled supramolecular architectures.

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Homoconjugation effects in triptycene based organic optoelectronic materials

Abstract: Triptycene is an archetypical homoconjugated molecule and an ideal substrate from which to learn what impact homoconjugation can have on useful molecular properties. This review highlights examples of triptycene based...

Cited by 19 publications

References 106 publications

Triptycene‐Fused Sterically Shielded Multi‐Resonance TADF Emitter Enables High‐Efficiency Deep Blue OLEDs with Reduced Dexter Energy Transfer

Triptycene‐Fused Sterically Shielded Multi‐Resonance TADF Emitter Enables High‐Efficiency Deep Blue OLEDs with Reduced Dexter Energy Transfer

Novel π-Extended Indolocarbazole-Based Deep-Blue Fluorescent Emitter with Remarkably Narrow Bandwidth for Solution-Processed Organic Light-Emitting Diodes

Homoconjugation and Tautomeric Isomerism in Triptycene-Fused Pyridylbenzimidazoles

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