Norbornadiene/Quadricyclane (
            <scp>NBD</scp>
            /
            <scp>QC</scp>
            ) and Conversion of Solar Energy

Orrego‐Hernández, Jessica; Hölzel, Helen; Wang, Zhihang; Quant, Maria; Moth‐Poulsen, Kasper

doi:10.1002/9783527827626.ch16

Cited by 7 publications

(5 citation statements)

References 62 publications

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“…Moreover, liquid MOST systems demand for heterogeneous catalysis to enable an energy release that proceeds fast enough. [31] The implementation into suitable storage devices then involves the tailoring of the combination of molecule system and appropriate catalyst for an optimized performance. Mechanistic insights into the surface processes during the reactions are needed in order to understand and improve the catalytic activity.…”

Section: Cycloreversion From Quadricyclane To Norbornadienementioning

confidence: 99%

The Norbornadiene/Quadricyclane Pair as Molecular Solar Thermal Energy Storage System: Surface Science Investigations

Hemauer,

Steinrück,

Papp

2024

ChemPhysChem

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For the transition to renewable energy sources, novel energy storage materials are more important than ever. This review addresses so‐called molecular solar thermal (MOST) systems, which appear very promising since they combine light harvesting and energy storing in one‐photon one‐molecule processes. The focus is on norbornadiene (NBD), a particularly interesting candidate, which is converted to the strained valence isomer quadricyclane (QC) upon irradiation. The stored energy can be released on demand. The energy‐releasing cycloreversion from QC to NBD can be initiated by a thermal, catalytic, or electrochemical trigger. The reversibility of the energy storage and release cycles determines the general practicality of a MOST system. In the search for derivatives, which enable large‐scale applications, fundamental surface science studies help to assess the feasibility of potential substituted NBD/QC couples. We focus on investigations under well‐defined ultra‐high vacuum (UHV) conditions as well as experiments in liquid phase. Next to mechanistic insights into the isomerization between the two valence isomers, information on adsorption geometries, thermal stability limits, and reaction pathways of the respective molecules are discussed. Moreover, laboratory‐scaled test devices demonstrated the proof of concept in various areas of application.

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Section: Cycloreversion From Quadricyclane To Norbornadienementioning

confidence: 99%

The Norbornadiene/Quadricyclane Pair as Molecular Solar Thermal Energy Storage System: Surface Science Investigations

Hemauer,

Steinrück,

Papp

2024

ChemPhysChem

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“…Typical examples include azobenzenes, hydrazones, , diarylethenes, , spiropyrans, and norbornadiene (NBD)/quadricyclane (QC) couples − based on E – Z isomerization, cyclization/retro cyclization, and C–C single and CC double bond rearrangement, respectively. Over the past few decades, significant research efforts have been devoted to investigating organic photoswitches that store photon energy in a meta -stable structure. − However, one major challenge is achieving photothermally reversible luminescence (PTRL) switching in the condensed phase instead of in solution, where the photothermal switches facilitate isomerization. Furthermore, established luminescent switches suffer from aggregation-induced quenching effects.…”

mentioning

confidence: 99%

“…Molecular photoswitches that undergo dynamic structural transformation between two photoisomers caused by alternate photo- or thermal stimulation are promising artificial photoswitching molecules as a result of their promising applications in optoelectronic devices, , bioimaging, , and super-resolution microscopy . Typical examples include azobenzenes, hydrazones, , diarylethenes, , spiropyrans, and norbornadiene (NBD)/quadricyclane (QC) couples − based on E – Z isomerization, cyclization/retro cyclization, and C–C single and CC double bond rearrangement, respectively. Over the past few decades, significant research efforts have been devoted to investigating organic photoswitches that store photon energy in a meta -stable structure. − However, one major challenge is achieving photothermally reversible luminescence (PTRL) switching in the condensed phase instead of in solution, where the photothermal switches facilitate isomerization.…”

mentioning

confidence: 99%

“…Therefore, it is imperative to design a new “smart” RTP switch (RTPS), which would address these limitations and create new opportunities in optoelectronics. Previously, molecular solar energy storage applications have been realized in NBD derivatives, where NBD photoisomerizes to a meta -stable structure (QC) that stores photon energy in chemical bonds. − However, to our knowledge, there are no reports on condensed-state RTP switching of NBD derivatives with visible light absorption. Herein, we demonstrate that such RTPS can be realized in NBD-functionalized donor–acceptor conjugates (CzN and TBCzN), where a benzonitrile acceptor (A) is covalently attached to the NBD unit via a C–C single bond and the carbazole donor (D) is held in a nearly orthogonal orientation with the A unit via a C–N single bond (Figure ).…”

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confidence: 99%

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Carbazole–Benzonitrile–Norbornadiene Conjugates for Photothermally Reversible Ambient Phosphorescence

Upadhyay,

Deka,

Ray

2024

J. Phys. Chem. Lett.

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Organic photoswitches have attracted significant attention across various fields, such as sensing, bioimaging, photopharmacology, molecular machines, and solar energy storage. However, as a result of design complexities, achieving photothermally reversible ambient phosphorescence switching in the condensed state remains elusive. Herein, we explore the impact of norbornadiene (NBD)/quadricyclane (QC) substitution at position 5 of the benzonitrile acceptor covalently attached to the carbazole donor on photothermally reversible luminescence switching. Experimental investigations demonstrated that the CzN and TBCzN switches exhibited photothermally reversible fluorescence switching in solution. Moreover, in the condensed state, fluorescence and ambient phosphorescence switching were observed as a result of a low singlet−triplet (ΔE ST ) gap (CzN ⇆ CzQ, ΔE ST CzN/CzQ = 0.05/0.28 eV; TBCzN ⇆ TBCzQ, ΔE ST TBCzN/TBCzQ = 0.06/0.09 eV). Reversible ambient phosphorescence switching is primarily influenced by modulation of acceptor conjugation resulting from NBD ⇆ QC switching. This approach may provide important clues for the design of visible-lightabsorbing photothermally reversible phosphorescent materials.

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“…To address this challenge, we present a new class of solidliquid biphasic catalysts that are optically activated and precipitated at a constant temperature (Figure 1b) by the incorporation of photoswitch units into the catalyst structure. A variety of photoswitches with diverse optical properties have been reported, e.g., spiropyran/merocyanine, [17] diarylethene, [18] azobenzene, [19] arylazopyrazole, [20] azothiophene, [21] hydrazone, [22] Stenhouse adduct, [23] norbornadiene/quadri cyclane (NBD/QC), [24] and dihydroazulene/ vinylheptafulvene (DHA/VHF), [25] which provide a wide collection of photoswitch units available to tailor the catalyst structure to various reaction conditions. The method of optical stimulation used to trigger these photoswitches presents a unique opportunity for regulating catalytic activity due to its non-invasive nature and high spaciotemporal resolution.…”

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confidence: 99%

Optically Controlled Recovery and Recycling of Homogeneous Organocatalysts Enabled by Photoswitches

et al. 2023

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We address a critical challenge of recovering and recycling homogeneous organocatalysts by designing photoswitchable catalyst structures that display a reversible solubility change in response to light. Initially insoluble catalysts are UV-switched to a soluble isomeric state, which catalyzes the reaction, then back-isomerizes to the insoluble state upon completion of the reaction to be filtered and recycled. The molecular design principles that allow for the drastic solubility change over 10 times between the isomeric states, 87 % recovery by the lightinduced precipitation, and multiple rounds of catalyst recycling are revealed. This proof of concept will open up opportunities to develop highly recyclable homogeneous catalysts that are important for the synthesis of critical compounds in various industries, which is anticipated to significantly reduce environmental impact and costs.

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Norbornadiene/Quadricyclane ( NBD / QC ) and Conversion of Solar Energy

Cited by 7 publications

References 62 publications

The Norbornadiene/Quadricyclane Pair as Molecular Solar Thermal Energy Storage System: Surface Science Investigations

The Norbornadiene/Quadricyclane Pair as Molecular Solar Thermal Energy Storage System: Surface Science Investigations

Carbazole–Benzonitrile–Norbornadiene Conjugates for Photothermally Reversible Ambient Phosphorescence

Optically Controlled Recovery and Recycling of Homogeneous Organocatalysts Enabled by Photoswitches

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