Photo‐/Baso‐Chromisms and the Application of a Dual‐Addressable Molecular Switch

Liu, Danyang; Yu, Binhong; Su, Xing; Wang, Xiaojun; Zhang, Yu‐Mo; Li, Minjie; Zhang, Sean Xiao‐An

doi:10.1002/asia.201900600

Cited by 9 publications

(3 citation statements)

References 52 publications

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“…E-FCA was found to be visibly fluorescent on the entire pH range studied (pH 2.0-12.0), with the maxima of the emission spectra being pH-dependent. Hence, although not characterized with significant fluorescence quantum yields, E-FCA might be considered as an acido-/basochromic fluorophore in a similar manner to some other compounds previously reported [41][42][43].…”

Section: Discussionmentioning

confidence: 83%

“…Instead, photoswitching between Z -FCA and E -FCA accompanied with psoralen pyrone ring-opening/closure in neutral to basic conditions could be noted. Considering the fact that the direction of photoisomerization is governed by protonation/deprotonation processes, the combined basochromic and photochromic behavior of Z / E -FCAs render them functional as a dual-responsive system [ 41 , 42 ].…”

Section: Discussionmentioning

confidence: 99%

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pH-Dependent Photoinduced Interconversion of Furocoumaric and Furocoumarinic Acids

et al. 2021

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Photo-controlled or photo-regulated molecules, especially biologically active and operating in physiological conditions, are in steady demand. Herein, furocoumaric and furocoumarinic acids being (Z/E)-isomers relative to each other were obtained in two stages starting from psoralen: the alkaline solvolysis of psoralen led to furocoumaric acid, which was further Z → E photoisomerized (365 nm) to furocoumarinic acid. The kinetics of Z → E photoisomerization was monitored by HPLC and UV-vis spectrophotometry. Photophysical characteristics in the aqueous phase for both acids, as well as the reversibility of (Z/E) photoisomerization process, were also assessed. Furocoumarinic acid was found to be visibly fluorescent at pH 2.0–12.0, with the maxima of fluorescence emission spectra being pH-dependent. The reverse E → Z photoisomerization predicted by quantum chemistry calculations as energetically favorable for the monoanionic form of furocoumarinic acid was proved in the experiment while being complicated by pyrone ring closure back to psoralen in acidic and neutral conditions. The preparative synthesis of furocoumarinic acid outlined in this work is particularly valuable in view of a wide range of pharmacological effects previously predicted for this compound.

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Section: Discussionmentioning

confidence: 83%

Section: Discussionmentioning

confidence: 99%

pH-Dependent Photoinduced Interconversion of Furocoumaric and Furocoumarinic Acids

et al. 2021

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“…The electronic and thermal free energies (E) of compound S1, S2, and S3 were −1679.65 KJ/mol, −1679.64 KJ/mol, and −1679.63 KJ/mol, respectively. The compound S1 had the lowest electronic and thermal free energies, indicating that S1 is more stable than S2 and S3 [38,39,40,41]. The high yield of the intramolecular cyclization reaction and deterministic structure indicates a high feasibility to synthesize the fully conjugated ladder polymers P3 and P6.…”

Section: Resultsmentioning

confidence: 99%

Simple Route to Synthesize Fully Conjugated Ladder Isomer Copolymers with Carbazole Units

et al. 2019

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Two isomer polymers, P3 and P6, with fully conjugated ladder structures are presented by simple synthetic routes. The well-defined structures of fully conjugated ladder polymers P3 and P6 were ensured by the high yields of every reaction step. The fully rigid ladder structures were confirmed by nuclear magnetic resonance (NMR), fourier transform infrared spectroscopy (FTIR), and photophysical test. Polymers P3 and P6 with bulky alkyl side chains exhibit good solution processability and desirable thermostable properties. After the intramolecular cyclization reaction, the band gaps of polymers P3 and P6 become lower (2.86 eV and 2.66 eV, respectively) compared with polymers P1 and P4. This initial study provides insight for the rational design of fully ladder-conjugated isomeric polymers with well-defined structures.

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Multi‐Photochromic Molecules Based on Dihydroazulene Units

Petersen

Hansen

Andreasen

et al. 2020

Chemistry A European J

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Multi-photochromic systemsi ncorporating individually addressables witching units are attractivef or development of advanced data storaged evices.H ere, we present the synthesis and properties of as election of such molecular systemsi ncorporating the dihydroazulene/vinylheptafulvene (DHA/VHF) photo-/thermoswitch. The influence of the linker (meta-phenylene vs. azulene-1,3-diyl vs. thiophene-2,5-diyl) separating two DHA units on the switching properties was investigated. An azulene-1,3-diyl spacer largely inhibited both the DHA-to-VHF photoisomerizations and the thermal VHF-to-DHA back-reactions;t he latter occurred ten times slower than for the related compound with a meta-phenyl-ene spacer.ADHA trimerc ontaining three DHA units aroundacentral benzene ring was found to undergo stepwise DHA-to-VHF photoisomerizations, whereas the thermal back-reactions occurred at similar rates for the three VHF entities.Ameta-phenylene-bridgedD HA dimerw as subjected to furthers tructural modifications at positionC-1 of each DHA,h avings trong implications for the switching events, and synthetic steps for further functionalizations at position C-7 of each DHA were investigated.F inally,t he molecular structure (from X-ray crystallographic analysis) between the meta-phenylene-bridgedDHA dimer and Cu I is presented.

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Photo‐/Baso‐Chromisms and the Application of a Dual‐Addressable Molecular Switch

Cited by 9 publications

References 52 publications

pH-Dependent Photoinduced Interconversion of Furocoumaric and Furocoumarinic Acids

pH-Dependent Photoinduced Interconversion of Furocoumaric and Furocoumarinic Acids

Simple Route to Synthesize Fully Conjugated Ladder Isomer Copolymers with Carbazole Units

Multi‐Photochromic Molecules Based on Dihydroazulene Units

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