Towards understanding the competition of electron and energy transfer in “molecular” nanographenes on the example of hexa-peri-hexabenzocoronene

Beneventi, Giovanni Mariano; Krug, Marcel; Reger, David; Jux, Norbert; Guldi, Dirk M.

doi:10.1016/j.jphotochemrev.2023.100602

Journal of Photochemistry and Photobiology C: Photochemistry Re

2023

DOI: 10.1016/j.jphotochemrev.2023.100602

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Towards understanding the competition of electron and energy transfer in “molecular” nanographenes on the example of hexa-peri-hexabenzocoronene

Giovanni Mariano Beneventi

Marcel Krug

David Reger

et al.

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2024

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Cited by 4 publications

(2 citation statements)

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“…The reduced η FRET at higher HBC concentrations implies the formation of HBC*•••HBC excimer, which not only hinders energy transfer but also quenches HBC emission. 28,77,78 In contrast, UMOF-2-X crystals exhibited a remarkable difference in the trend in η FRET (Figure 3e and Table S4). UMOF-2-X (X = 7, 14, 18, and 39) showcased η FRET values of 21%, 45%, 46%, and 47%, respectively.…”

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confidence: 97%

“…The most significant decrease in HPB lifetime was observed for the HPB:HBC = 1:0.1 solution upon photoexcitation at 310 nm, which exhibited the highest η FRET of 69% (Figure S23 and Table S3). The reduced η FRET at higher HBC concentrations implies the formation of HBC*···HBC excimer, which not only hinders energy transfer but also quenches HBC emission. ,, In contrast, UMOF-2- X crystals exhibited a remarkable difference in the trend in η FRET (Figure e and Table S4). UMOF-2- X ( X = 7, 14, 18, and 39) showcased η FRET values of 21%, 45%, 46%, and 47%, respectively.…”

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confidence: 97%

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Unveiling Energy Transfer Mechanisms in Nanographene-Incorporated Metal–Organic Frameworks

Lee,

Hwang,

Kim

et al. 2024

ACS Materials Lett.

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Nanographenes are a class of extended πconjugated molecules with great potential for photophysical and electrochemical properties. However, most nanographenes show self-aggregation due to their strong π−π interaction, resulting in structures barely possessing any open π surface. We find that metal−organic frameworks (MOFs) can be an ideal platform to construct periodic arrays and pores with isolated large π-conjugated surfaces by avoiding undesired π−π interactions between the nanographene molecules. Here, we report a multivariate series of nanographene-incorporated MOFs, UMOF-2-X, utilizing the graphene-like hexatopic organic linkers, hexaphenylethynylbenzene (HPB) and hexabenzocoronene (HBC), through a mixed-linker strategy. Remarkably, UMOF-2 inhibits the occurrence of linker-to-metal charge transfer to Cu metal and shows efficient energy transfer between HPB and HBC linkers.

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confidence: 97%

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confidence: 97%

Unveiling Energy Transfer Mechanisms in Nanographene-Incorporated Metal–Organic Frameworks

Lee,

Hwang,

Kim

et al. 2024

ACS Materials Lett.

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Laterally π‐Extensed Nitrogen‐Doped Molecular Nanographenes – From Anti‐Kasha Emission to Ping‐Pong Energy Transfer Events

Beneventi,

Schöll,

Platzer

et al. 2024

Advanced Energy Materials

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Nanographenes, which feature at least one dimension smaller than 100 nm, are drawing interdisciplinary attention. Understanding the interplay between structure and properties is, however, still in its infancy. Molecular nanographenes are much better suited to fill this knowledge gap than graphene quantum dots or nanoribbons. Their bottom‐up synthesis allows atomic precision and, thereby, assists in handling structure and connecting it with properties. Herein, the effects of nitrogen‐doping and lateral π‐extension in molecular nanographenes and in their coordination complexes with ruthenium porphyrins are investigated. The presence of just nitrogen resulted in an increase of the fluorescence quantum yield, without, however, affecting the energy levels. Lateral π‐extension of the nanographenes, instead, resulted in a modulation of the excited states energy, which leads to a thermally‐activated dual fluorescence with quantum yields as high as 61%. In the corresponding coordination complexes, lateral π‐extension resulted in a ping‐pong energy transfer cascade, that is, from the nanographene to the metalloporphyrin and back to the nanographene. The results help to directly rationalize properties observed in both graphene quantum dots and nanoribbons. Moreover, they prove that molecular nanographenes are appealing components for solar energy conversion schemes, where the modulation of inter‐component energy transfer is of utmost importance.

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Boron‐ and Oxygen‐Doped π‐Extended Helical Nanographene with Circularly Polarised Thermally Activated Delayed Fluorescence

Venugopal,

Kumar,

Badrinarayan Jadhav

et al. 2024

Chemistry A European J

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Helical nanographenes have garnered substantial attention owing to their finely adjustable optical and semiconducting properties. The strategic integration of both helicity and heteroatoms into the nanographene structure, facilitated by a boron‐oxygen‐based multiple resonance (MR) thermally activated delayed fluorescence (TADF), elevates its photophysical and chiroptical features. This signifies the introduction of an elegant category of helical nanographene that combines optical (TADF) and chiroptical (CPL) features. In this direction, we report the synthesis, optical, and chiroptical properties of boron, oxygen‐doped ᴨ‐extended helical nanographene. The π‐extension induces distortion in the DOBNA‐incorporated nanographene, endowing a pair of helicenes, (P)‐B2NG, and (M)‐B2NG exhibiting circularly polarized luminescence with glum of ‐2.3 × 10−3 and +2.5 × 10−3, respectively. B2NG exhibited MR‐TADF with a lifetime below 5 μs, and a reasonably high fluorescence quantum yield (50%). Our molecular design enriches the optical and chiroptical properties of nanographenes and opens up new opportunities in multidisciplinary fields.

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Towards understanding the competition of electron and energy transfer in “molecular” nanographenes on the example of hexa-peri-hexabenzocoronene

Cited by 4 publications

References 143 publications

Unveiling Energy Transfer Mechanisms in Nanographene-Incorporated Metal–Organic Frameworks

Unveiling Energy Transfer Mechanisms in Nanographene-Incorporated Metal–Organic Frameworks

Laterally π‐Extensed Nitrogen‐Doped Molecular Nanographenes – From Anti‐Kasha Emission to Ping‐Pong Energy Transfer Events

Boron‐ and Oxygen‐Doped π‐Extended Helical Nanographene with Circularly Polarised Thermally Activated Delayed Fluorescence

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