Fusing perylene diimide with helicenes

Bao, Si Tong; Jiang, Haoyu; Jin, Zexin; Nuckolls, Colin

doi:10.1002/chir.23561

Cited by 8 publications

(6 citation statements)

References 75 publications

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“…It is favorable for them to be excellent donoracceptor hybrids with promising applications in electronic and optoelectronic devices. [12][13][14][15] The study of nonlinear optical (NLO) properties of PMDI-, NTCDI-, and PTCDI-based materials has received much attention. [16][17][18][19][20][21][22] For example, a series of zinc porphyrin (ZnP)-perylene diimide (PDI) molecules were proven to exhibit excellent second-order NLO properties.…”

Section: Introductionmentioning

confidence: 99%

“…They have planar π‐framework and are easily functionalized. It is favorable for them to be excellent donor‐acceptor hybrids with promising applications in electronic and optoelectronic devices [12–15] . The study of nonlinear optical (NLO) properties of PMDI‐, NTCDI‐, and PTCDI‐based materials has received much attention [16–22] .…”

Section: Introductionmentioning

confidence: 99%

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Electronic and Nonlinear Optical Properties of B(III)‐Submonoazaporphyrin‐π‐Diimide Compounds: A Density Functional Theory Study

Liu,

Hou

2024

ChemPhysChem

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Three hypothetical complexes were designed using diimides (PMDI, NTCDI and PTCDI) as the acceptor unit and B(III)‐submonoazaporphyrin (1) as the donor unit. These complexes have smaller HOMO‐LUMO energy gaps (3.39‐3.96 eV) than pristine 1 (6.61 eV). Further, the energy gap can be tuned by changing the number of benzene rings of these diimides. Remarkably, these proposed complexes possess considerable first hyperpolarizabilities (β0) (4865‐6921 a.u.), and the regularity of the β0 values remained the same in the gas phase and toluene solvent conditions. There is an inverse relationship between the energy gap and the polarizability/first hyperpolarizability. In addition, absorption spectra, frontier molecular orbitals, and hole electron distributions were obtained using time‐dependent density functional theory calculations to emphasize the relationship between structure and properties. Ultraviolet‐Visible absorption spectra reveals that all complexes show satisfying IR working regions. Further analysis of the first hyperpolarizability density reveals the nature of the excellent NLO properties of the studied systems. This study can provide valuable insights for the development of potential high‐performance NLO molecules.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Electronic and Nonlinear Optical Properties of B(III)‐Submonoazaporphyrin‐π‐Diimide Compounds: A Density Functional Theory Study

Liu,

Hou

2024

ChemPhysChem

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“…Polycyclic aromatic hydrocarbons (PAHs) including azulene, 1 perylene diimide (PDI), 2 diketopyrrolopyrrole (DPP), 3 and indenofluorenes 4 have attracted tremendous attention owing to their attractive optoelectronic properties and applications in organic field effect transistors, organic synapses, and organic thermoelectric materials. 5–10 Rubicene (C 26 H 14 ) is a 26-π-electron and planar PAH, which has been known for over 100 years. 11,12 In recent years, this red compound has received increasing attention due to its unique optoelectronic properties, including high electron affinity, and highly fluorescent and photostable properties.…”

Section: Introductionmentioning

confidence: 99%

The design, synthesis and application of rubicene based polycyclic aromatic hydrocarbons (PAHs)

Ma,

Han,

Shi

et al. 2023

J. Mater. Chem. C

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“…We recently reported a new type of dynamic, axial chirality in perylene diimide (PDI)-based twistacenes, − where remote chiral substituents on the imide position control the helicity of the aromatic core. Here, we describe the chiroptical switching of a new c hPDI[2] derivative by manipulating the multiple redox states of the PDI subunits (Figure a).…”

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confidence: 99%

Near-Infrared, Organic Chiroptic Switch with High Dissymmetry Factors

Bao,

Louie,

Jiang

et al. 2023

J. Am. Chem. Soc.

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Here we unveil a chiral molecular redox switch derived from PDI-based twistacenes�chPDI[2] that has the remarkable attributes of high-intensity and a broadband chiral response. This material exhibits facile, stable, and reversible multistate chiroptical switching behavior over a broad active wavelength range close to 700 nm, encompassing ultraviolet, visible, and nearinfrared regions. Upon reduction, chPDI[2] exhibits a substantial increase in the amplitude of its circular dichroic response, with an outstanding |ΔΔε| > 300 M −1 cm −1 and a high dissymmetry factor of 3 × 10 −2 at 960 nm. DFT calculations suggest that the long wavelength CD signal for doubly reduced chPDI [2] originates from excitation of the PDI backbone to the π* orbital of the bridging alkene. Importantly, the dimer's molecular contortion facilitates ionic diffusion, enabling chiral switching in solid state films. The high dissymmetry factors and near-infrared response establish chPDI[2] as a unique chiroptic switch.

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Fusing perylene diimide with helicenes

Cited by 8 publications

References 75 publications

Electronic and Nonlinear Optical Properties of B(III)‐Submonoazaporphyrin‐π‐Diimide Compounds: A Density Functional Theory Study

Electronic and Nonlinear Optical Properties of B(III)‐Submonoazaporphyrin‐π‐Diimide Compounds: A Density Functional Theory Study

The design, synthesis and application of rubicene based polycyclic aromatic hydrocarbons (PAHs)

Near-Infrared, Organic Chiroptic Switch with High Dissymmetry Factors

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