Continuous synthesis of pyridocarbazoles and initial photophysical and bioprobe characterization

McQuade, D. Tyler; O’Brien, Alexander G.; Dörr, Markus; Rajaratnam, Rajathees; Eisold, Ursula; Monnanda, Bopanna; Nobuta, Tomoya; Löhmannsröben, Hans‐Gerd; Meggers, Eric; Seeberger, Peter H.

doi:10.1039/c3sc51846a

Cited by 14 publications

(8 citation statements)

References 32 publications

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“…The popular capillary photomicroreactor assembly was used for a variety of photocyclizations, such as the synthesis of pyridocarbazole ligands,65 phenanthrenes and helicenes,66 and tetrahydroquinolines 67. The same design was also used for the scalable photobromination of 5‐methylpyrimidine in flow to yield 5‐bromomethylpyrimidine, a precursor of Rosuvastatin 68.…”

Section: Photochemistry In Continuous‐flow Reactorsmentioning

confidence: 99%

Photochemical Transformations Accelerated in Continuous‐Flow Reactors: Basic Concepts and Applications

Straathof

Hessel

et al. 2014

Chemistry A European J

454

271

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Continuous-flow photochemistry is used increasingly by researchers in academia and industry to facilitate photochemical processes and their subsequent scale-up. However, without detailed knowledge concerning the engineering aspects of photochemistry, it can be quite challenging to develop a suitable photochemical microreactor for a given reaction. In this review, we provide an up-to-date overview of both technological and chemical aspects associated with photochemical processes in microreactors. Important design considerations, such as light sources, material selection, and solvent constraints are discussed. In addition, a detailed description of photon and mass-transfer phenomena in microreactors is made and fundamental principles are deduced for making a judicious choice for a suitable photomicroreactor. The advantages of microreactor technology for photochemistry are described for UV and visible-light driven photochemical processes and are compared with their batch counterparts. In addition, different scale-up strategies and limitations of continuous-flow microreactors are discussed.

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Section: Photochemistry In Continuous‐flow Reactorsmentioning

confidence: 99%

Photochemical Transformations Accelerated in Continuous‐Flow Reactors: Basic Concepts and Applications

Straathof

Hessel

et al. 2014

Chemistry A European J

454

271

View full text Add to dashboard Cite

show abstract

“…The FEP reactor concept has now been used and adapted for a number of reactions, resulting in the synthesis of a wide range of complex, photochemically derived products. [19][20][21][22][23][24][25][26][27][28] Perhaps the most striking of these has been the use of an FEP flow reactor in the scaled-up continuous synthesis of the frontline anti-malarial drug artemisinin described by Seeberger and co-workers. [29,30] Many groups have now reported the advantages of flow photochemistry over previously reported batch results.…”

Section: Introductionmentioning

confidence: 99%

Batch versus Flow Photochemistry: A Revealing Comparison of Yield and Productivity

Elliott

Knowles

Koovits

et al. 2014

Chemistry A European J

182

120

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The use of flow photochemistry and its apparent superiority over batch has been reported by a number of groups in recent years. To rigorously determine whether flow does indeed have an advantage over batch, a broad range of synthetic photochemical transformations were optimized in both reactor modes and their yields and productivities compared. Surprisingly, yields were essentially identical in all comparative cases. Even more revealing was the observation that the productivity of flow reactors varied very little to that of their batch counterparts when the key reaction parameters were matched. Those with a single layer of fluorinated ethylene propylene (FEP) had an average productivity 20% lower than that of batch, whereas three-layer reactors were 20% more productive. Finally, the utility of flow chemistry was demonstrated in the scale-up of the ring-opening reaction of a potentially explosive [1.1.1] propellane with butane-2,3-dione.

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“…Moreover, a π-π* transition absorption band appears at 370 nm, as well as a forbidden n-π* band at 430 nm, implying the formation of cis-azobenzene [42,43]. Two isobestic points become visible, demonstrating that complexes 1 and 2 undergo photoisomerization from E-isomer to Z-isomer [44][45][46][47]. Fig.…”

Section: Third-order Nlo Switching Properties Of the Metal Complexesmentioning

confidence: 90%

Third-order nonlinear optical adjusting behavior in azobenzene metal complexes

et al. 2020

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The third-order nonlinear optical (NLO) materials with stimuli-responsive properties have received extraordinary attention due to their controllable photophysical properties. In this work, two attractive metal complexes thirdorder NLO switches, which are far superior to congeneric optical switches in terms of their performance conversion, versatility, and fast response, were successfully designed and synthesized. The test of their third-order NLO properties proves that the metal complexes exhibit reverse saturable absorption and self-defocusing refraction. After light irradiation, the third-order NLO behavior turns quickly into selffocusing refraction. The relation between the molecular structures and the third-order NLO properties was investigated via 1 H nuclear magnetic resonance and ultravioletvisible absorption. The results show that the metal ions have a significant influence on the NLO behavior and reveal the origin of third-order NLO properties via Z-scan determinations, pump-probe technology, and density functional theory calculations. These metal complexes can be used as third-order NLO switches with excellent fatigue resistance and broaden the application range of third-order NLO materials with adjustable performances.

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Continuous synthesis of pyridocarbazoles and initial photophysical and bioprobe characterization

Cited by 14 publications

References 32 publications

Photochemical Transformations Accelerated in Continuous‐Flow Reactors: Basic Concepts and Applications

Photochemical Transformations Accelerated in Continuous‐Flow Reactors: Basic Concepts and Applications

Batch versus Flow Photochemistry: A Revealing Comparison of Yield and Productivity

Third-order nonlinear optical adjusting behavior in azobenzene metal complexes

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