Polycyclic aromatic hydrocarbons containing heavy group 14 elements: From synthetic challenges to optoelectronic devices

Delouche, Thomas; Hissler, Muriel; Bouit, Pierre‐Antoine

doi:10.1016/j.ccr.2022.214553

Cited by 23 publications

(18 citation statements)

References 74 publications

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“…Next to the trisilapentathia [8]circulene (Si-3A in Figure 6) based on the suflower molecule, there is another potential Si-3A molecule that is derived from a trisilasumanene 50 (a [6]circulene compound), as shown Figure 12. Also, Ge and Sn anchor elements can be inserted at the position of silicon in the sumanene molecules, as shown in a study by Bouit et al 51 3.2. Lantern Organic Framework Nanotube.…”

Section: Resultsmentioning

confidence: 99%

Computational Design of a Lantern Organic Framework

Nguyen

Truong

2023

ACS Omega

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This study employed a computational quantum chemistry approach to design lantern organic framework (LOF) materials. Using the density functional theory method with the B3LYP-D3/6-31+G(d) level theory, novel lantern molecules ranging from two to eight bridges made of sp3 and sp carbon atoms to connect circulene bases that have phosphorous or silicon as anchor atoms were made. It was found that five-sp3-carbon and four-sp-carbon bridges are optimal candidates for constructing the lantern framework in the vertical direction. Although circulenes can be stacked vertically, their resulting HOMO–LUMO gaps remain relatively unchanged, indicating their potential applications as porous materials and for host–guest chemistry. The electrostatic potential surface maps reveal that LOF materials are relatively electrostatically neutral overall.

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Section: Resultsmentioning

confidence: 99%

Computational Design of a Lantern Organic Framework

Nguyen

Truong

2023

ACS Omega

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“…Polycyclic aromatic hydrocarbon (PAH) derivatives with electron-rich or electron-poor functional groups can promote the electron or hole transport in comparison to PAH molecules and have attracted wide attention due to their prospects in electronic and optoelectronic devices. − In this paper, we select the electron-rich ketone PAH derivative pyrene-4,5,9,10-tetraone (PT) molecules as the organic ligands to explore their phase transition as well as functionalization since ketone groups can be employed to form not only hydrogen bonds but also metal–organic coordination bonds. The Au(111) surface is used as the substrate for phase transition considering that the ketone groups have the abilities to lift the underlying gold atoms and provide possibilities for the phase transition induced by metal atoms.…”

Section: Introductionmentioning

confidence: 99%

Structural Phase Transition of Quinone-Containing PAH Derivatives on Au(111) at High Coverage

et al. 2023

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Delicate control over structural phase transition provides advanced approaches for the fabrication of the desired well-ordered nanoarchitectures on surfaces. The participation of intrinsic metal adatoms in pure organic systems can facilitate the structural phase transition by direct capture of surface metal adatoms and forming metal–organic bonds. However, most of the situations occur at low coverage; such structural phase transition at a higher molecular concentration is limited to some extent due to the poor migration ability. Thus, high-concentration phase transition needs to be explored, which might be significant for the design and exploitation of large-scale ordered metal–organic-related nanomaterials. Herein, we report the phase transition of pyrene-4,5,9,10-tetraone (PT) molecules at high coverage (∼1 monolayer (ML)) on Au(111) from hydrogen-bonded row-like nanostructures to metal–organic honeycomb networks by coordinating with surface Au adatoms as demonstrated by scanning tunneling microscopy (STM). Combined with density functional theory (DFT) calculations, we demonstrate that identical molecular density (or unit cells) of two nanostructures should be the key, which makes it possible to realize phase transition possibly by in situ rotation and coordinating with the gold adatoms. Also, the phase transition causes the modulation of electronic properties from semiconductive ones to metallic ones.

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“…A variety of heteroatoms, especially those of groups 13–15, containing π-conjugated molecules, have become inherent molecules in various research fields spanning from fundamental chemistry to functional material chemistry and supramolecular chemistry. − The introduction of the heteroatoms changes the electronic structures of the π-conjugated molecules due to the interaction of the atomic orbitals of the heteroatoms with the π orbitals of the parent hydrocarbons. Triarylborane is a representative molecule exhibiting unique electron-deficient characteristics. − Bridging one adjacent ortho – ortho position of the phenyl groups with heteroatoms is an attractive strategy to integrate the orbital interactions of the heteroatoms into the parent skeletons.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Azadioxa-Planar Triphenylboranes Bridged by Aryl- and Alkylimino Groups and Their Photophysical Properties

et al. 2023

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Heteroatom-bridged planar triphenylboranes, in which the three phenyl groups are bridged at the ortho positions by heteroatoms, are attracting growing attention as one of the heteroatom-containing π-conjugated molecules. Herein, we developed the synthetic method of planar triphenylboranes bridged by two oxygen atoms and one nitrogen atom, and the substituent on the nitrogen atom is derived into various aryl and alkyl groups. A key intermediate bearing an imino group (−NH−) was synthesized from a bis-triflate precursor bridged by two oxo groups via a nucleophilic aromatic substitution reaction of benzyl amine and following debenzylation. The X-ray crystallographic analysis revealed that the compound exhibits a planar molecular structure which can form a one-dimensionally π-stacked structure. The photophysical and density functional theory studies revealed that their highest occupied molecular orbitals and lowest unoccupied molecular orbitals (LUMOs) are originated from the triphenylborane moiety, while introducing strong electron-withdrawing groups such as the 4-cyanophenyl group on the nitrogen atom can induce the localization of the LUMO at the aryl groups instead of the triphenylborane moiety.

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Polycyclic aromatic hydrocarbons containing heavy group 14 elements: From synthetic challenges to optoelectronic devices

Cited by 23 publications

References 74 publications

Computational Design of a Lantern Organic Framework

Computational Design of a Lantern Organic Framework

Structural Phase Transition of Quinone-Containing PAH Derivatives on Au(111) at High Coverage

Synthesis of Azadioxa-Planar Triphenylboranes Bridged by Aryl- and Alkylimino Groups and Their Photophysical Properties

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