Clar Rules the Electronic Properties of 2D π‐Conjugated Frameworks: Mind the Gap

Strutyński, Karol; Mateo‐Alonso, Aurelio; Melle‐Franco, Manuel

doi:10.1002/chem.201905087

Cited by 8 publications

(4 citation statements)

References 62 publications

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“…Increasing the pore size of 2D FANs would allow the diffusion and encapsulation of organic, inorganic and biological macromolecules and would make available materials that combine both larger band gaps [14] and porosities, broadening the application scope of 2D FANs into other fields, such as sensing and heterogeneous catalysis. However, synthesising 2D FANs with larger dimensions is a difficult task.…”

Section: Introductionmentioning

confidence: 99%

An Expanded 2D Fused Aromatic Network with 90‐Ring Hexagons

et al. 2021

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Two-dimensional fused aromatic networks (2D FANs) have emerged as ah ighly versatile alternative to holey graphene.T he synthesis of 2D FANs with increasingly larger lattice dimensions will enable new application perspectives.H owever,t he synthesis of larger analogues is mostly limited by lack of appropriate monomers and methods.Herein, we describe the synthesis,characterisation and properties of an expanded 2D FANw ith 90-ring hexagons,w hiche xceed the largest 2D FANl attices reported to date.

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Section: Introductionmentioning

confidence: 99%

An Expanded 2D Fused Aromatic Network with 90‐Ring Hexagons

et al. 2021

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“…Density functional theory( DFT) computed key values of the building blocks are also highlighted to establish relationships between their electronic properties and the resulting porous framework properties. It must be noted that we have performed theoretical calculations using the B3LYP/def2-TZVP [41] level of theory to calculate the frontier orbitals (HOMO and LUMO) for the different organic building blocks included in Table 1. Importantly,t he structures and electronic properties of porous materials may be adjusted by the judiciouss election and combination of the electroactiveb uilding blocks and appropriate functionalization.…”

Section: Introductionmentioning

confidence: 99%

Electroactive Organic Building Blocks for the Chemical Design of Functional Porous Frameworks (MOFs and COFs) in Electronics

Souto

Strutyński

Melle‐Franco

et al. 2020

Chemistry A European J

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Electroactive organic molecules have received a lot of attention in the field of electronics because of their fascinating electronic properties, easy functionalization and potential low cost towards their implementation in electronic devices. In recent years, electroactive organic molecules have also emerged as promising building blocks for the design and construction of crystalline porous frameworks such as metal–organic frameworks (MOFs) and covalent‐organic frameworks (COFs) for applications in electronics. Such porous materials present certain additional advantages such as, for example, an immense structural and functional versatility, combination of porosity with multiple electronic properties and the possibility of tuning their physical properties by post‐synthetic modifications. In this Review, we summarize the main electroactive organic building blocks used in the past few years for the design and construction of functional porous materials (MOFs and COFs) for electronics with special emphasis on their electronic structure and function relationships. The different building blocks have been classified based on the electronic nature and main function of the resulting porous frameworks. The design and synthesis of novel electroactive organic molecules is encouraged towards the construction of functional porous frameworks exhibiting new functions and applications in electronics.

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“…Over almost a half of a century, Gutman and his coworkers contributed in development of the Kekulé‐ and Clar‐structure based approaches which can be successfully applied to rationalize the π‐electron structure, and to predict many physical properties and chemical behavior of PAHs [42–44] . According to the Clar theory, [45,46] fully benzenoid hydrocarbons are the most stable benzenoids, and a number of these molecules has been synthesized [4,10,47] . The charged N‐doped PAHs ( 1N – 3N3 ) studied in this work are expected to have the same number of π electrons as their parent fully benzenoid molecules ( 1 – 3 ).…”

Section: Introductionmentioning

confidence: 99%

“…[42][43][44] According to the Clar theory, [45,46] fully benzenoid hydrocarbons are the most stable benzenoids, and a number of these molecules has been synthesized. [4,10,47] The charged N-doped PAHs (1N-3N3) studied in this work are expected to have the same number of π electrons as their parent fully benzenoid molecules (1)(2)(3). The position of N-atoms in 1N-3N3 was selected based on commonly used strategies in the synthesis of PAHs.…”

Section: Introductionmentioning

confidence: 99%

Tuning the Structure and Properties of N‐doped Positively Charged Polycyclic Aromatic Hydrocarbons

Radenković

Tomović

2022

ChemPhysChem

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This work is dedicated to the seminal contributions of Professor Klaus Müllen and Professor Ivan Gutman to science and on the occasion of their 75th birthday.A detailed study of the geometry, aromatic character, electronic and magnetic properties for a series of positively charged Ndoped polycyclic aromatic hydrocarbons (PAHs) was performed. Magnetic properties of the examined molecules were analyzed by means of the magnetically induced current density calculated using the diamagnetic-zero version of the continuous transformation of origin of current density (CTOCD-DZ) method. The comparative study of the local aromaticity of the studied molecules was performed using several different indices: energy effect (ef), harmonic oscillator model of aromaticity (HOMA) index, six centre delocalization index (SCI) and nucleus independent chemical shifts (NICS). The presence of N-atoms in the inner rings was found to cause a planarity distortion in the studied N-doped systems. The geometric changes and charged nature of the studied N-doped systems do not significantly influence the current density and the local aromaticity distribution in comparison with the corresponding parent benzenoid hydrocarbons. The present study demonstrates how quantum chemical calculations can be used for rational design of novel PAHs and for fine tuning of their properties.

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Clar Rules the Electronic Properties of 2D π‐Conjugated Frameworks: Mind the Gap

Cited by 8 publications

References 62 publications

An Expanded 2D Fused Aromatic Network with 90‐Ring Hexagons

An Expanded 2D Fused Aromatic Network with 90‐Ring Hexagons

Electroactive Organic Building Blocks for the Chemical Design of Functional Porous Frameworks (MOFs and COFs) in Electronics

Tuning the Structure and Properties of N‐doped Positively Charged Polycyclic Aromatic Hydrocarbons

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