Tailored Design of π-Extended Multi-Resonance Organoboron using Indolo[3,2-b]Indole as a Multi-Nitrogen Bridge
Tianjiao Fan1, Senqiang Zhu2, Xudong Cao3
1Key Lab of Organic Optoelectronics and Molecular Engineering of Ministry of Education, Department of Chemistry, Tsinghua University, 100084, Beijing, P. R. China.
Abstract:
Extending the π-skeletons of multi-resonance (MR) organoboron emitters can feasibly modulate their optoelectronic properties. Here, we first adopt the indolo[3,2-b]indole (32bID) segment as a multi-nitrogen bridge and develop a high-efficiency π-extended narrowband green emitter. This moiety establishes not only a high-yield one-shot multiple Bora-Friedel-Crafts reaction towards a π-extended MR skeleton, but a compact N-ethylene-N motif for a red-shifted narrowband emission. An emission peak at 524 nm, a small full width at half maximum of 25 nm and a high photoluminescence quantum yield of 96 % are concurrently obtained in dilute toluene. The extended molecular plane also results in a large horizontal emitting dipole orientation ratio of 87 %. A maximum external quantum efficiency (EQE) of 36.6 % and a maximum power efficiency of 135.2 lm/W are thereafter recorded for the corresponding device, also allowing a low efficiency roll-off with EQEs of 34.5 % and 28.1 % at luminance of 1,000 cd/m2 and 10,000 cd/m2 , respectively.
More Related Videos
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Resonance and Hybrid Structures
Resonance Structures and Resonance Hybrids
The Lewis structure of a nitrite anion (NO2−) may actually be drawn in two different ways, distinguished by the locations of the N–O and N=O bonds.
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
π Molecular Orbitals of 1,3-Butadiene
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
Resonance
Exceptions to the Octet Rule
