In this study, a new class of photo- and thermochromic compounds was discovered. Fluorescent dihydropyridazine-appended dibenzosuberenone derivatives with central seven-membered rings were converted to colorless spiro anthrones with central six-membered rings by thermal isomerization or visible-light (420 nm) irradiation. Under UV light (350 nm), the spiro anthrones converted back to benzosuberenones. The chemical structures of the spiro anthrones were determined by NMR, UV-vis spectroscopy, and HRMS analyses. It was also observed that the dibenzosuberenone derivatives were oxidized on exposure to UV irradiation for a long time.
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http://dx.doi.org/10.1021/acs.orglett.1c01413 | DOI Listing |
Org Lett
September 2024
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao, Shandong 266003, People's Republic of China.
Six new angucycline structures, including spirocyclione A (), which contains an unusual oxaspiro[5.5]undecane architecture, and its ring-A-cleaved product spirocyclione B (), were discovered by heterologous expression of a type II polyketide biosynthetic gene cluster captured from a marine actinomycete strain sp. HDN155000.
View Article and Find Full Text PDFEur J Med Chem
December 2023
Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008, India; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India. Electronic address:
A series of Rhodamine type Anthrone-Spirolactam (ASL) derivatives Benzylimin-Anthrone-Spirolactam (ASL-1 to ASL-10) and Benzamide-Anthrone-Spirolactam (ASL-11 and ASL-12) were synthesized via a simple condensation reaction between Anthrone Spiro-lactamine (2) and various aromatic aldehyde and acyl chlorides respectively. Since rhodamine-based compounds were reported to have antiviral activity, the ASL derivatives were examined for in vitro antiviral activity against dengue and chikungunya viruses. Among all the analogues, ASL-3, ASL-6, ASL-7, ASL-8, ASL-9 and ASL-10 were the most potent against dengue virus (DENV) and exerted around one log reduction in virus titre under post-treatment conditions.
View Article and Find Full Text PDFOrg Lett
June 2021
Department of Chemistry, Faculty of Sciences, Atatürk University, Erzurum 25240, Turkey.
In this study, a new class of photo- and thermochromic compounds was discovered. Fluorescent dihydropyridazine-appended dibenzosuberenone derivatives with central seven-membered rings were converted to colorless spiro anthrones with central six-membered rings by thermal isomerization or visible-light (420 nm) irradiation. Under UV light (350 nm), the spiro anthrones converted back to benzosuberenones.
View Article and Find Full Text PDFJ Phys Chem A
August 2019
Laser Research Centre, Faculty of Physics , Vilnius University, Sauletekio 10 , LT10223 Vilnius , Lithuania.
The phenomenon of the intramolecular triplet-triplet (T-T) energy transfer observed for spiro[9,10-dihydro-9-oxoanthracene-10,2'-5',6'-benzindan] () molecule was investigated using stationary and time-resolved techniques in the UV/vis spectral region. The rate constant for energy transfer from anthrone chromophore to the triplet state localized on the naphthalene subunit of molecule is 2.8 × 10 s.
View Article and Find Full Text PDFJ Org Chem
June 2013
State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China.
Photoinduced reactions of bicyclopropylidene (BCP) with para-quinones (p-quinones) including benzoquinones, naphthoquinones, and anthraquinones were found to proceed via different cycloaddition pathways and lead to diverse polycyclic products bearing spiropropyl moiety. Photocycloaddition of BCP with benzoquinones gave spirooxetanes as the primary products, which upon irradiation were able to rearrange into the spiro[4.5]deca-6,9-diene-2,8-diones as secondary photoproducts.
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