2020
DOI: 10.1002/chem.202002649
|View full text |Cite
|
Sign up to set email alerts
|

Concise Approach to T‐Shaped NBN‐Phenalene Cored Luminogens as Intensive Blue Light Emitters

Abstract: Small organic molecules with finely tunable physical properties are highlyd esired for the fabricationo fl owcost and high-performance organic electronic devices.Int his work, the syntheses of as eries of T-shaped NBN-embedded dibenzophenalene derivatives throught he formationo fa key brominated intermediate in as toichiometrically controlled reactiona re presented. The geometrica nd electronic structures of these T-shaped molecules can be simply tailored by attaching substituents along the direction perpendic… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1
1
1

Citation Types

0
5
0

Year Published

2022
2022
2024
2024

Publication Types

Select...
7

Relationship

0
7

Authors

Journals

citations
Cited by 9 publications
(5 citation statements)
references
References 48 publications
(36 reference statements)
0
5
0
Order By: Relevance
“…In recent years, three heteroatoms (X-B-X; X = O, N, S) incorporated polycyclic aromatic hydrocarbons were prepared. Their optical and photophysical studies were carried out by various research groups of Hatakeyama, Müllen, Helten, Zhang, and others. , These molecules have more extended delocalization, and their electronic structure cannot be directly compared with phenalenes. Ma, Zhao, and co-workers recently developed synthetic methods for NBN-doped phenalenes.…”
Section: Boron-doped Phenalenyl Molecules and Their Derivativesmentioning
confidence: 99%
“…In recent years, three heteroatoms (X-B-X; X = O, N, S) incorporated polycyclic aromatic hydrocarbons were prepared. Their optical and photophysical studies were carried out by various research groups of Hatakeyama, Müllen, Helten, Zhang, and others. , These molecules have more extended delocalization, and their electronic structure cannot be directly compared with phenalenes. Ma, Zhao, and co-workers recently developed synthetic methods for NBN-doped phenalenes.…”
Section: Boron-doped Phenalenyl Molecules and Their Derivativesmentioning
confidence: 99%
“…X-ray diffraction analysis of single crystals of 6 (solvent: CHCl 3 , antisolvent: MeOH) showed a nearly planar structure of the NBN-dibenzophenalene scaffold (maximum deviation from planarity: 6.0°), with each azaborine ring depicting a slight distortion, likely originated by repulsion between the peri - N -mesityl groups (Figure ). The B–N bond lengths of 1.438 and 1.448 Å denote a partial double bond character, as previously observed with other peripherally doped NBN-containing PAHs. ,,,, X-ray analysis of terarylene 1 Ph (solvent: toluene, antisolvent: MeOH) showed two crystallographically independent molecules, both displaying a planar polyaromatic core (maximum deviation from planarity: 1.7°–2.8°), in the asymmetric unit, and B–N bond lengths for the NBN unit (1.438–1.450 Å) consistent with those measured for derivative 6 . The peripheral azaborine-like B–N bond lengths fall within the 1.413–1.421 Å range, suggesting a distinct double bond character that is peculiar to 9,10-azaboraphenanthrenes (see SI, section 4, for 5 Me , 5 Ph , and 5 Mes ).…”
Section: Resultsmentioning
confidence: 96%
“…The B−N bond lengths of 1.438 and 1.448 Å denote a partial double bond character, as previously observed with other peripherally doped NBN-containing PAHs. 23,32,33,55,56 X-ray analysis of terarylene 1 Ph (solvent: toluene, antisolvent: MeOH) showed two crystallographically independent molecules, both displaying a planar polyaromatic core (maximum deviation from planarity: 1.7°−2.8°), in the asymmetric unit, and B−N bond lengths for the NBN unit (1.438−1.450 Å) consistent with those measured for derivative 6. The peripheral azaborine-like B−N bond lengths fall within the 1.413−1.421 Å range, suggesting a distinct double bond character that is peculiar to 9,10-azaboraphenanthrenes 57−60 (see SI, section 4, for 5 Me , 5 Ph , and 5 Mes ).…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…The strong second-order NLO responses of these butterfly-shaped nanographenes under external fields, particularly sum frequency generation, could provide promising potential applications in exploring molecular structure and charging at interfaces in materials science. [30] A clear understanding of the effects of each functional moiety on the NLO properties on a molecular level helps in the design of novel NLO materials for applications in organic field-effect transistors, [2,32] organic light-emitting diodes, [33] and organic photovoltaics devices. [34] The aggregation pattern of these butterfly-shaped nanographenes deserves further exploration to search for higherperformance NLO functional materials for practical application.…”
Section: Chemistry-a European Journalmentioning
confidence: 99%