Pyrene Functionalized Norbornadiene-Quadricyclane Fluorescent Photoswitches: Characterization of their Spectral Properties and Application in Imaging of Amyloid Beta Plaques.

This study presents the synthesis and characterization of two fluorescent norbornadiene (NBD) photoswitches, each incorporating two conjugated pyrene units. Expanding on the limited repertoire of reported photoswitchable fluorescent NBDs, we explore their properties with a focus on applications in bioimaging of amyloid beta (Aß) plaques. While the fluorescence emission of the NBD decreases upon photoisomerization, aligning with what has been previously reported, for the first time we observed luminescence after irradiation of the quadricyclane (QC) isomer. We deduce how the observed emission is induced by photoisomerization to the excited state of the parent isomer (NBD) which is then the emitting species. Thorough characterizations including NMR, UV-Vis, fluorescence, X-ray structural analysis and density functional theory (DFT) calculations provide a comprehensive understanding of these systems. Notably, one NBD-QC system exhibits exceptional durability. Additionally, these molecules serve as effective fluorescent stains targeting Aß plaques in situ, with observed NBD/QC switching within the plaques. Molecular docking simulations explore NBD interactions with amyloid, unveiling novel binding modes. These insights mark a crucial advancement in the comprehension and design of future photochromic NBDs for bioimaging applications and beyond, emphasizing their potential in studying and addressing protein aggregates.

Multichromophoric photoswitches for solar energy storage: from azobenzene to norbornadiene, and MOST things in between.

The ever-increasing global demands for energy supply and storage have led to numerous research efforts into finding and developing renewable energy technologies. Molecular solar thermal energy storage (MOST) systems utilise molecular photoswitches that can be isomerized to a metastable high-energy state upon solar irradiation. These high-energy isomers can then be thermally or catalytically converted back to their original state, releasing the stored energy as heat on-demand, offering a means of emission-free energy storage from a closed system, often from only organic materials. In this context, multichromophoric systems which incorporate two or more photochromic units may offer additional functionality over monosubstituted analogues, due to their potential to access multiple states as well as having more attractive physical properties. The extended conjugation offered by these systems can lead to a red shift in the absorption profile and hence a better overlap with the solar spectrum. Additionally, the multichromophoric design may lead to increased energy storage densities due to some of the molecular weight being 'shared' across several energy storage units. This review provides an overview and analysis of multichromophoric photoswitches incorporating the norbornadiene/quadricyclane (NBD/QC) couple, azobenzene (AZB), dihydroazulene (DHA) and diarylethene (DAE) systems, in the context of energy storage applications. Mixed systems, where two or more different chromophores are linked together in one molecule, are also discussed, as well as limitations such as the loss of photochromism due to inner filter effects or self-quenching, and how these challenges may be overcome in future designs of multichromophoric systems.

Synthesis and Characterization of Carbon-Based Heterogeneous Catalysts for Energy Release of Molecular Solar Thermal Energy Storage Materials.

Molecular solar thermal energy storage (MOST) systems are rapidly becoming a feasible alternative to energy storage and net-zero carbon emission heating. MOST systems involve a single photoisomerization pair that incorporates light absorption, storage, and heat release processes in one recurring cycle. Despite significant recent advancements in the field, the catalytic back-reaction from MOST systems remains relatively unexplored. A wide range of applications is possible, contingent on the energy densities of the specific photoisomers. Here, we report platinum-, copper-, and nickel-based heterogeneous catalysts screened in batch conditions for the back-conversion reaction on the cyano-3-(4-methoxyphenyl)-norbornadiene/quadricyclane pair. Catalyst reactivities are investigated using structural characterization, imaging techniques, and spectroscopic analysis. Finally, the thermal stability is also explored for our best-performing catalysts.

Unveiling the Potential of Heterogeneous Catalysts for Molecular Solar Thermal Systems.

Solar energy utilization has gained considerable attention due to its abundance and renewability. However, its intermittent nature presents a challenge in harnessing its full potential. The development of energy storing compounds capable of capturing and releasing solar energy on demand has emerged as a potential solution. These compounds undergo a photochemical transformation that results in a high-energy metastable photoisomer, which stores solar energy in the form of chemical bonds and can release it as heat when required. Such systems are referred to as MOlecular Solar Thermal (MOST)-systems. Although the photoisomerization of MOST systems has been vastly studied, its back-conversion, particularly using heterogeneous catalysts, is still underexplored and the development of effective catalysts for releasing stored energy is crucial. Herein we compare the performance of 27 heterogeneous catalysts releasing the stored energy in an efficient Norbornadiene/Quadricyclane (NBD/QC) MOST system. We report the first benchmarking of heterogeneous catalysts for a MOST system using a robust comparison method of the catalysts' activity and monitoring the conversion using UV-Visible (UV-Vis) spectroscopy. Our findings provide insights into the development of effective catalysts for MOST systems. We anticipate that our assay will reveal the necessity of further investigation on heterogeneous catalysis.

Flow-Integrated Preparation of Norbornadiene Precursors for Solar Thermal Energy Storage.

Molecular solar thermal (MOST) energy storage systems are getting increased attention related to renewable energy storage applications. Particularly, 2,3-difunctionalized norbornadiene-quadricyclane (NBD-QC) switches bearing a nitrile (CN) group as one of the two substituents are investigated as promising MOST candidates thanks to their high energy storage densities and their red-shifted absorbance. Moreover, such NBD systems can be prepared in large quantities (a requirement for MOST-device applications) in flow through Diels-Alder reaction between cyclopentadiene and appropriately functionalized propynenitriles. However, these acetylene precursors are traditionally prepared in batch from their corresponding acetophenones using reactive chemicals potentially leading to health and physical hazards, especially when working on a several-grams scale. Here, we develop a multistep flow-chemistry route to enhance the production of these crucial precursors. Furthermore, we assess the atom economy (AE) and the E-factor showing improved green metrics compared to classical batch methods. Our results pave the way for a complete flow synthesis of NBDs with a positive impact on green chemistry aspects.

The statistical probability factor in triplet mediated photon upconversion: a case study with perylene.

Triplet-triplet annihilation photon upconversion (TTA-UC) is a process where two low-energy photons are converted into one higher-energy photon. A crucial component for an efficient upconversion process is the statistical probability factor (f), defined as the probability of the formation of a high-energy singlet state upon coupling of two low-energy triplet states. Theoretically, f depends on the energy level distribution, molecular orientation, inter-triplet exchange coupling of triplet dyads, and spin-mixing of resulting spin states (singlet, triplet, and quintet). However, experimental values of f for acene-based annihilators have been subject to large variations due to many factors that have resulted in the reporting of different f values for the same molecule. In this work, we discuss these factors by studying perylene as a case study annihilator, for which by far the largest variation in f = 16 to 100% has been reported. We systematically investigated the TTA-UC of PdTPBP:perylene, as a sensitizer-annihilator pair and obtained the experimental f = 17.9 ± 2.1% for perylene in THF solution. This limits the maximum TTA-UC quantum yield to 9.0% (out of 50%) for this annihilator. We found that such a low f value for perylene is largely governed by the energy-gap law where higher non-radiative losses due to the small energy gap between 2 × T1 and T2 affect the probability of singlet formation. Interestingly, we found this observation true for other acene-based annihilators whose emission ranges from the UV to the yellow region, thus providing a blueprint for future design of efficient TTA-UC systems.

Site Selectivity of Peptoids as Azobenzene Scaffold for Molecular Solar Thermal Energy Storage.

Storing solar energy is a key challenge in modern science. MOlecular Solar Thermal (MOST) systems, in particular those based on azobenzene switches, have received great interest in the last decades. The energy storage properties of azobenzene (t1/2 <4 days; ΔH~270 kJ/kg) must be improved for future applications. Herein, we introduce peptoids as programmable supramolecular scaffolds to improve the energy storage properties of azobenzene-based MOST systems. We demonstrate with 3-unit peptoids bearing a single azobenzene chromophore that dynamics of the MOST systems can be tuned depending on the anchoring position of the photochromic unit on the macromolecular backbone. We measured a remarkable increase of the half-life of the metastable form up to 14 days at 20 °C for a specific anchoring site, significantly higher than the isolated azobenzene moiety, thus opening new perspectives for MOST development. We also highlight that liquid chromatography coupled to mass spectrometry does not only enable to monitor the different stereoisomers during the photoisomerization process as traditionally done, but also allows to determine the thermal back-isomerization kinetics.

Bulky Substituents Promote Triplet-Triplet Annihilation Over Triplet Excimer Formation in Naphthalene Derivatives.

Visible-to-ultraviolet (UV) triplet-triplet annihilation photochemical upconversion (TTA-UC) has gained a lot of attention recently due to its potential for driving demanding high-energy photoreactions using low-intensity visible light. The efficiency of this process has rapidly improved in the past few years, in part thanks to the recently discovered annihilator compound 1,4-bis((triisopropylsilyl)ethynyl)naphthalene (N-2TIPS). Despite its beneficial TTA-UC characteristics, the success of N-2TIPS in this context is not yet fully understood. In this work, we seek to elucidate what role the specific type and number of substituents in naphthalene annihilator compounds play to achieve the characteristics sought after for TTA-UC. We show that the type of substituent attached to the naphthalene core is crucial for its performance as an annihilator. More specifically, we argue that the choice of substituent dictates to what degree the sensitized triplets form excimer complexes with ground state annihilators of the same type, which is a process competing with that of TTA. The addition of more bulky substituents positively impacts the upconverting ability by impeding excimer formation on the triplet surface, an effect that is enhanced with the number of substituents. The presence of triplet excimers is confirmed from transient absorption measurements, and the excimer formation rate is quantified, showing several orders of magnitude differences between different derivatives. These insights will aid in the further development of annihilator compounds for solar energy applications for which the behavior at low incident powers is of particular significance.

Efficient degassing and ppm-level oxygen monitoring flow chemistry system.

Low oxygen levels are critical for a long range of chemical transformations carried out in both flow and batch chemistry. Here, we present an inline continuous flow degassing system based on a gas-permeable membrane inside a vacuum chamber for achieving and monitoring ppm-level oxygen concentrations in solutions. The oxygen presence was monitored with a molecular oxygen probe and a continuously running UV-vis spectrometer. An automated setup for discovering optimal reaction conditions for minimal oxygen presence was devised. The parameters tested were: flow rate, vacuum pressure, solvent back-pressure, tube material, tube length and solvent oxygen solubility. The inline degassing system was proven to be effective in removing up to 99.9% of ambient oxygen from solvents at a flow rate of 300 µl min-1 and 4 mbar vacuum pressure inside the degassing chamber. Reaching lower oxygen concentrations was limited by gas permeation in the tubing following the degassing unit, which could be addressed by purging large volume flow reactors with an inert gas after degassing or by using tubing with lower gas permeability, such as stainless steel tubing. Among all factors, oxygen solubility in solvents was found to play a significant role in achieving efficient degassing of solvents. The data presented here can be used to choose optimal experimental parameters for oxygen-sensitive reactions in flow chemistry reaction setups. The data were also fitted to an analytically derived model from simple differential equations in physical context of the experiment.

The Effect of the Pd Precursors on the Shape of Hollow Ag-Pd Alloy Nanoparticles Using Ag Nanocubes as Seeds.

Hollow Ag-Pd nanoparticles have potentially high catalytic performance owing to their larger surface area compared to their corresponding solid nanoparticles. We successfully fabricated hollow Ag-Pd alloy nanodendrites and nanoboxes by using different Pd precursors (H2PdCl4 and Pd(acac)2) to achieve large surface area nanoboxes. Interestingly, the use of a H2PdCl4 precursor led to the formation of hollow nanodendrite structures, whereas the slower reduction of Pd(acac)2 led to the formation of hollow nanoboxes. The microstructure and chemical composition of Ag-Pd nanoparticles and properties of their growth solutions were investigated by transmission electron microscopy, energy-dispersive X-ray spectroscopy, and ultraviolet-visible spectroscopy.

Searching the Chemical Space of Bicyclic Dienes for Molecular Solar Thermal Energy Storage Candidates.

Photoswitches are molecular systems that are chemically transformed subsequent to interaction with light and they find potential application in many new technologies. The design and discovery of photoswitch candidates require intricate molecular engineering of a range of properties to optimize a candidate to a specific applications, a task which can be tackled efficiently using quantum chemical screening procedures. In this paper, we perform a large scale screening of approximately half a million bicyclic diene photoswitches in the context of molecular solar thermal energy storage using ab initio quantum chemical methods. We further device an efficient strategy for scoring the systems based on their predicted solar energy conversion efficiency and elucidate potential pitfalls of this approach. Our search through the chemical space of bicyclic dienes reveals systems with unprecedented solar energy conversion efficiencies and storage densities that show promising design guidelines for next generation molecular solar thermal energy storage systems.

Searches for bridged bicyclic molecules in space-norbornadiene and its cyano derivatives.

The norbornadiene (NBD) molecule, C7H8, owes its fame to its remarkable photoswitching properties that are promising for molecular solar-thermal energy storage systems. Besides this photochemical interest, NBD is a rather unreactive species within astrophysical conditions and it should exhibit high photostability, properties that might also position this molecule as an important constituent of the interstellar medium (ISM)-especially in environments that are well shielded from short-wavelength radiation, such as dense molecular clouds. It is thus conceivable that, once formed, NBD can survive in dense molecular clouds and act as a carbon sink. Following the recent interstellar detections of large hydrocarbons, including several cyano-containing ones, in the dense molecular cloud TMC-1, it is thus logical to consider searching for NBD-which presents a shallow but non-zero permanent electric dipole moment (0.06 D)-as well as for its mono- and dicyano-substituted compounds, referred to as CN-NBD and DCN-NBD, respectively. The pure rotational spectra of NBD, CN-NBD, and DCN-NBD have been measured at 300 K in the 75-110 GHz range using a chirped-pulse Fourier-transform millimetre-wave spectrometer. Of the three species, only NBD was previously studied at high resolution in the microwave domain. From the present measurements, the derived spectroscopic constants enable prediction of the spectra of all three species at various rotational temperatures (up to 300 K) in the spectral range mapped at high resolution by current radio observatories. Unsuccessful searches for these molecules were conducted toward TMC-1 using the QUIJOTE survey, carried out at the Yebes telescope, allowing derivation of the upper limits to the column densities of 1.6 × 1014 cm-2, 4.9 × 1010 cm-2, and 2.9 × 1010 cm-2 for NBD, CN-NBD, and DCN-NBD, respectively. Using CN-NBD and cyano-indene as proxies for the corresponding bare hydrocarbons, this indicates that-if present in TMC-1-NBD would be at least four times less abundant than indene.

Triplet-triplet annihilation mediated photon upconversion solar energy systems.

Solar energy harvesting is among the best solutions for a global transition toward carbon-neutral energy technologies. The existing solar energy harvesting technologies like photovoltaics (PV) and emerging molecular concepts such as solar fuels and molecular solar thermal energy storage (MOST) are rapidly developing. However, to realize their full potential, fundamental solar energy loss channels like photon transmission, recombination, and thermalization need to be addressed. Triplet-triplet annihilation mediated photon upconversion (TTA-UC) is emerging as a way to overcome losses due to the transmission of photons below the PV/chromophore band gap. However, there are several challenges related to the integration of efficient solid-state TTA-UC systems into efficient devices such as: wide band absorption, materials sustainability, and device architecture. In this article, we review existing work, identify and discuss challenges as well as present our perspective toward possible future directions.

Bulk-Processed Plasmonic Plastic Nanocomposite Materials for Optical Hydrogen Detection.

ConspectusSensors are ubiquitous, and their importance is only going to increase across many areas of modern technology. In this respect, hydrogen gas (H2) sensors are no exception since they allow mitigation of the inherent safety risks associated with mixtures of H2 and air. The deployment of H2 technologies is rapidly accelerating in emerging energy, transport, and green steel-making sectors, where not only safety but also process monitoring sensors are in high demand. To meet this demand, cost-effective and scalable routes for mass production of sensing materials are required. Here, the state-of-the-art often resorts to processes derived from the microelectronics industry where surface-based micro- and nanofabrication are the methods of choice and where (H2) sensor manufacturing is no exception.In this Account, we discuss how our recent efforts to develop sensors based on plasmonic plastics may complement the current state-of-the-art. We explore a new H2 sensor paradigm, established through a series of recent publications, that combines (i) the plasmonic optical H2 detection principle and (ii) bulk-processed nanocomposite materials. In particular, plasmonic plastic nanocomposite sensing materials are described that comprise plasmonic H2-sensitive colloidally synthesized nanoparticles dispersed in a polymer matrix and enable the additive manufacturing of H2 sensors in a cost-effective and scalable way. We first discuss the concept of plasmonic plastic nanocomposite materials for the additive manufacturing of an active plasmonic sensing material on the basis of the three key components that require individual and concerted optimization: (i) the plasmonic sensing metal nanoparticles, (ii) the surfactant/stabilizer molecules on the nanoparticle surface from colloidal synthesis, and (iii) the polymer matrix. We then introduce the working principle of plasmonic H2 detection, which relies on the selective absorption of H species into hydride-forming metal nanoparticles that, in turn, induces distinct changes in their optical plasmonic signature in proportion to the H2 concentration in the local atmosphere. Subsequently, we assess the roles of the key components of a plasmonic plastic for H2 sensing, where we have established that (i) alloying Pd with Au and Cu eliminates hysteresis and introduces intrinsic deactivation resistance at ambient conditions, (ii) surfactant/stabilizer molecules can significantly accelerate and decelerate H2 sorption and thus sensor response, and (iii) polymer coatings accelerate sensor response, reduce the limit of detection (LoD), and enable molecular filtering for sensor operation in chemically challenging environments. Based on these insights, we discuss the rational development and detailed characterization of bulk-processed plasmonic plastics based on glassy and fluorinated matrix polymers and on tailored flow-chemistry-based synthesis of Pd and PdAu alloy colloidal nanoparticles with optimized stabilizer molecules. In their champion implementation, they enable highly stable H2 sensors with response times in the 2 s range and an LoD of few 10 ppm of H2. To put plasmonic plastics in a wider perspective, we also report their implementation using different polymer matrix materials that can be used for 3D printing and (an)isotropic Au nanoparticles that enable the manufacturing of macroscopic plasmonic objects with, if required, dichroic optical properties and in amounts that can be readily upscaled. We advertise that melt processing of plasmonic plastic nanocomposites is a viable route toward the realization of plasmonic objects and sensors, produced by scalable colloidal synthesis and additive manufacturing techniques.

Protein cohabitation: long-term immunoglobulin G storage at room temperature.

Long-term functional storage of therapeutic proteins at room temperature has been an eternal challenge. Inspired by the cellular cooperativity of proteins, we have taken a step forward to address this challenge by cohabitating Immunoglobulin G (IgG1) with a food protein gelatin in the solid-state at room temperature. Interestingly, IgG1 remained functionally active for a record 14 months revealed from the western-blot assay. Further quantification by HP-LC analysis showed 100% structural integrity of IgG1 with no degradation in the gelatin matrix during this period. The developed formulation has a direct application in oral medical nutrition therapy to cure gastrointestinal microbial infections. Also the strategy provides a robust energy economic alternative to the protein engineering methods for long-term functional storage of therapeutic proteins at room temperature.

Investigating New Applications of a Photoswitchable Fluorescent Norbornadiene as a Multifunctional Probe for Delineation of Amyloid Plaque Polymorphism.

Amyloid beta (Aß) plaques are a major pathological hallmark of Alzheimer's disease (AD) and constitute of structurally heterogenic entities (polymorphs) that have been implicated in the phenotypic heterogeneity of AD pathology and pathogenesis. Understanding amyloid aggregation has been a critical limiting factor to gain understanding of AD pathogenesis, ultimately reflected in that the underlying mechanism remains elusive. We identified a fluorescent probe in the form of a turn-off photoswitchable norbornadiene derivative (NBD1) with several microenvironment-sensitive properties that make it relevant for applications within advanced fluorescence imaging, for example, multifunctional imaging. We explored the application of NBD1 for in situ delineation of structurally heterogenic Aß plaques in transgenic AD mouse models. NBD1 plaque imaging shows characteristic broader emission bands in the periphery and more narrow emission bands in the dense cores of mature cored plaques. Further, we demonstrate in situ photoisomerization of NBD1 to quadricyclane and thermal recovery in single plaques, which is relevant for applications within both functional and super-resolution imaging. This is the first time a norbornadiene photoswitch has been used as a probe for fluorescence imaging of Aß plaque pathology in situ and that its spectroscopic and switching properties have been studied within the specific environment of senile Aß plaques. These findings open the way toward new applications of NBD-based photoswitchable fluorescent probes for super-resolution or dual-color imaging and multifunctional microscopy of amyloid plaque heterogeneity. This could allow to visualize Aß plaques with resolution beyond the diffraction limit, label different plaque types, and gain insights into their physicochemical composition.

Far-red triplet sensitized Z-to-E photoswitching of azobenzene in bioplastics.

We report the first example of direct far-red triplet sensitized molecular photoswitching in a condensed phase wherein a liquid azobenzene derivative (Azo1) co-assembled within a liquid surfactant-protein film undergoes triplet sensitized Z-to-E photoswitching upon far-red/red light excitation in air. The role of triplet sensitization in photoswitching has been confirmed by quenching of sensitizer phosphorescence by Z-Azo1 and temperature-dependent photoswitching experiments. Herein, we demonstrate new biosustainable fabrication designs to address key challenges in solid-state photoswitching, effectively mitigating chromophore aggregation and requirement of high energy excitations by dispersing the photoswitch in the trapped liquid inside the solid framework and by shifting the action spectrum from blue-green light (450-560 nm) to the far-red/red light (740/640 nm) region.

High throughput screening of norbornadiene/quadricyclane derivates for molecular solar thermal energy storage.

We present a procedure for performing high throughput screening of molecular compounds for molecular solar thermal energy storage devices using extended tight binding (xTB) methods. In order to validate our approach, we performed screening of 3230 norbornadiene/quadricyclane (NBD/QC) derivatives in terms of storage energies, activation barriers and absorption of solar radiation using our approach, and compared it to high level density functional theory (DFT) and cluster perturbation (CP) theory calculations. Our comparisons show that the xTB screening framework correlates very well with DFT and CP theory in that it predicts the same relative trends in the studied parameters although the storage energies and thermal reaction barriers are significantly offset. Utilizing the screening methodology, we have been able to locate compounds that would either be excellent candidates or compounds that should not be considered further for molecular solar thermal energy storage devices. This methodology can readily be extended and applied to screening other molecular motifs for molecular solar energy storage.

Recyclable optical bioplastics platform for solid state red light harvesting via triplet-triplet annihilation photon upconversion.

Sustainable photonics applications of solid-state triplet-triplet annihilation photon upconversion (TTA-UC) are limited by a small UC spectral window, low UC efficiency in air, and non-recyclability of polymeric materials used. In a step to overcome these issues, we have developed new recyclable TTA-UC bioplastics by encapsulating TTA-UC chromophores liquid inside the semicrystalline gelatin films showing broad-spectrum upconversion (red/far-red to blue) with high UC efficiency in air. For this, we synthesized a new anionic annihilator, sodium-TIPS-anthracene-2-sulfonate (TIPS-AnS), that combined with red/far-red sensitizers (PdTPBP/Os(m-peptpy)2(TFSI)2), a liquid surfactant Triton X-100 reduced (TXr) and protein gelatin (G) formed red/far-red to blue TTA-UC bioplastic films just by air drying of their aqueous solutions. The G-TXr-TIPS-AnS-PdTPBP film showed record red to blue (633 to 478 nm) TTA-UC quantum yield of 8.5% in air. The high UC quantum yield has been obtained due to the fluidity of dispersed TXr containing chromophores and oxygen blockage by gelatin fibers that allowed efficient diffusion of triplet excited chromophores. Further, the G-TXr-TIPS-AnS-Os(m-peptpy)2(TFSI)2 bioplastic film displayed far-red to blue (700-730 nm to 478 nm) TTA-UC, demonstrating broad-spectrum photon harvesting. Finally, we demonstrated the recycling of G-TXr-TIPS-AnS-PdTPBP bioplastics by developing a downstream approach that gives new directions for designing future recyclable photonics bioplastic materials.

Photolytic Studies of Norbornadiene Derivatives under High-Intensity Light Conditions.

The photoconversion of a norbornadiene (NBD) derivative was studied under high-intensity mono- and polychromatic light conditions at high concentrations. The photoisomerization quantum yield (ϕNBD→QC), proceeding from NBD to its quadricyclane (QC) isomer, was determined using a tunable OPO laser and a solar simulator light source. The solar simulator was designed to mimic the AM1.5G solar spectrum between 300 and 900 nm. Using the OPO laser, ϕNBD→QC was measured at discrete values between 310 and 350 nm in steps of 10 nm, and a variation between 0.81 and 0.96 was observed. Weighting these values of ϕNBD→QC with the spectral profile of the solar simulator, an averaged value of 0.87 ± 0.03 was obtained. Determination of ϕNBD→QC was also performed directly in the solar simulator providing a value of 0.97 ± 0.14, in good agreement with the weighted values from the OPO. Photoisomerization quantum yields were found to decrease slightly at higher concentrations. At high concentrations, we found that correcting for the presence of QC was important due to similar absorption coefficients of the NBD and QC isomers at the absorption tail. Cyclability of the forward and backward NBD/QC conversion was studied over several cycles. The NBD/QC couple exhibited excellent thermal stability, but a slight photodegradation per cycle was observed, increasing with the concentration of the sample. This result indicates that the molecules undergo some intermolecular reactions.