Hierarchical Self-Assembly of Perylene Diimide (PDI) Crystals

Kim, Yong-Jae; Lee, Yonghee; Park, Kangho; Ahn, Chi Won; Jung, Hee‐Tae; Jeon, Hwan‐Jin

doi:10.1021/acs.jpclett.0c01226

Cited by 24 publications

(17 citation statements)

References 46 publications

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“…We know that the PBI skeleton is typically modified at its imide, bay, and/or ortho positions. Unlike bay or ortho substituents, functionalization at the imide positions has a negligible or limited influence on the photophysical properties, while this strategy provides a benefit for enhancing their solubility and impeding their aggregations. ,, In detail, the spectra were characterized by three well-resolved vibronic bands with a splitting on the order of Δ ṽ = 1370 cm –1 (Δ E = 0.17 eV) coupled with the vibration of the perylene skeleton, and the band intensity decreased in the sequence of transitions 0–0 (522 nm) > 0–1 (486 nm) > 0–2 (456 nm), which is typical for the absorption characteristics of monomeric PBI. ,− The molar extinction coefficient (ε) increases obviously with increasing the efficient π-conjugation, especially the obvious change from 8.14 × 10 4 M –1 ·cm –1 of PCP-PBI to 1.28 × 10 5 M –1 ·cm –1 of CB-PBI (Tables S1–S4). Their fluorescence spectra exhibit broad emission with maximum emission wavelengths around 530 nm, confirming the presence of monomeric PBI.…”

Section: Results and Discussionmentioning

confidence: 99%

Resonance-Enhanced Two-Photon Absorption and Optical Power Limiting Properties of Three-Dimensional Perylene Bisimide Derivatives

et al. 2021

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Push−pull organic structures characterized by an intramolecular charge transfer (ICT) process and π-electron delocalization are potentially interesting luminescent materials. A series of three-dimensional o-carborane-containing perylene bisimide derivatives (PBIs) were synthesized, and their optical properties were systematically investigated to illustrate the stereo effect, especially on the two-photon absorption (2PA) and optical power limiting (OPL) properties. Open-aperture Z-scan curves showed that all four PBIs displayed strong and broad two-photon absorptivities based on the resonance-enhanced phenomenon. The maximum degenerate two-photon absorption cross section (δ 2PA ) increased with the number of PBI substituents. The derivative CB-PBI possessed a δ 2PA value of ∼2400 GM at 650 nm, a significant enhancement in comparison with that of the parent PBI (∼719 GM), ascribed to the present stereo effect. When the aromatic-donating units changed from naphthyl and pyrenyl to PBI, the generated multidimensional intramolecular charge transfer (ICT) from the aromatic units to the o-carborane cage contributed to the 2PA processes. All of the fluorophores exhibited excellent optical power limiting (OPL) performances as well as a minimum limiting threshold of ∼4.98 mJ/cm 2 for CB-PBI. These significant results not only allow us to get deep insight into the nature of the fundamental stereo effect and nonlinear optical (NLO) response involved but also guide us toward the design of new multifunctional luminescent materials.

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Section: Results and Discussionmentioning

confidence: 99%

Resonance-Enhanced Two-Photon Absorption and Optical Power Limiting Properties of Three-Dimensional Perylene Bisimide Derivatives

et al. 2021

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“…To this end, one effective strategy is to design PDI acceptors with controllable self-assembly properties. 13,14 The assembly of aromatic-fused π-conjugated molecules is a powerful tool to calibrate and enhance their optoelectronic properties for applications in OSCs, organic field-effect transistors (OFETs), and organic light-emitting diodes (OLEDs). Understanding the preferred molecular assembly is a requisite for constructing a predictive guideline for developing novel materials with exaggerated performance.…”

Section: Introductionmentioning

confidence: 99%

Symmetry-Induced Orderly Assembly Achieving High-Performance Perylene Diimide-Based Nonfullerene Organic Solar Cells

et al. 2021

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Controllable assembly of organic semiconductors has opened an avenue for an in-depth perception of their structure-property relationships; however, a detailed investigation of their molecular controllability remains challenging. Discerning the assembly of organic semiconductors could enable the attainment of a significant improvement of performance. Here, we report the fabrication of efficient nonfullerene organic solar cells (OSCs) based on two isomeric perylene diimide (PDI)fused corannulene acceptors, namely, corannurylene pentapetalae (CRP). A single-crystal analysis demonstrated that differentially symmetric isomers such as CRP-1 and CRP-2 display various assembly framework structures. Both isomeric CRP acceptor-based solar cells showed excellent power conversion efficiencies matching a medium bandgap polymer donor (P3TEA). Compared with CRP-2, a high symmetry-induced orderly assembly endowed CRP-1 with a higher efficiency of 11.2%, which is the maximum performance of PDI-based OSCs reported to date. This study sheds light on designing high-performance organic semiconductors allowing for symmetric orderly assembly.

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“…Missing these pieces of the structural puzzle means that orientation of molecules in the aggregated state remains unknown. Organic particles which exhibit nanocrystalline order potentially overcome this problem by exploiting X-ray diffraction, 44–47 however, nanocrystals constitute a small percentage of the thousands of reported organic aggregates formed from solution. 48–55…”

Section: Introductionmentioning

confidence: 99%

Multiple aggregates from multiple polymorphs: structural and mechanistic insight into organic dye aggregates

Hogan

Sutherland

2022

Nanoscale

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Hierarchical Self-Assembly of Perylene Diimide (PDI) Crystals

Cited by 24 publications

References 46 publications

Resonance-Enhanced Two-Photon Absorption and Optical Power Limiting Properties of Three-Dimensional Perylene Bisimide Derivatives

Resonance-Enhanced Two-Photon Absorption and Optical Power Limiting Properties of Three-Dimensional Perylene Bisimide Derivatives

Symmetry-Induced Orderly Assembly Achieving High-Performance Perylene Diimide-Based Nonfullerene Organic Solar Cells

Multiple aggregates from multiple polymorphs: structural and mechanistic insight into organic dye aggregates

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