Abstract:Photochemical reaction is a chemical reaction initiated by the absorption of energy in the form of light resulting in different types of reaction. Chromones, bischromones and anthraquinones are the bichromophoric molecules which contain the carbonyl group and double bond in conjugation. Photochemical reactions of these compounds result in the formation of such molecules which are not obtained via conventional methods. This review article describes the photochemical transformations of chromones, bischromones an… Show more
“…Among them, chromone moiety has been used in the design of various colorimetric chemosensors for detecting copper ion [35][36][37][38][39]. The chromone moiety has unique spectral properties and great photostability because of the chromophoric units of chromone having C═C and C═O [40,41]. On the other hand, compounds such as pyrrole, furan, and thiophene can act as electron donors or receptors, thus enhancing charge transfer by binding to metal ions.…”
A colorimetric chemosensor CMF (N′‐[(E)‐(4‐oxo‐4H‐chromen‐3‐yl)methylidene]furan‐2‐carbohydrazide) was applied for detecting Cu2+. CMF showed colorimetric selectivity to Cu2+ through a color variation from colorless to yellow. Binding ratio between CMF and Cu2+ was analyzed by Job plot to be a 2:1. Limit of detection was found to be 0.38 μM. The practicality of CMF was illustrated by the quantification of Cu2+ in real samples. In particular, the CMF‐coated test kit was able to detect the copper ions at a concentration lower than the recommended concentration (31.5 μM) of the World Health Organization (WHO) for copper ion. The binding mode of CMF and copper ions was studied through UV–visible spectroscopy, 1H NMR titration, ESI‐mass analysis, and DFT calculations. Sensing mechanism of CMF to Cu2+ was proposed to be the ligand‐to‐metal charge transfer (LMCT) through DFT calculations.
“…Among them, chromone moiety has been used in the design of various colorimetric chemosensors for detecting copper ion [35][36][37][38][39]. The chromone moiety has unique spectral properties and great photostability because of the chromophoric units of chromone having C═C and C═O [40,41]. On the other hand, compounds such as pyrrole, furan, and thiophene can act as electron donors or receptors, thus enhancing charge transfer by binding to metal ions.…”
A colorimetric chemosensor CMF (N′‐[(E)‐(4‐oxo‐4H‐chromen‐3‐yl)methylidene]furan‐2‐carbohydrazide) was applied for detecting Cu2+. CMF showed colorimetric selectivity to Cu2+ through a color variation from colorless to yellow. Binding ratio between CMF and Cu2+ was analyzed by Job plot to be a 2:1. Limit of detection was found to be 0.38 μM. The practicality of CMF was illustrated by the quantification of Cu2+ in real samples. In particular, the CMF‐coated test kit was able to detect the copper ions at a concentration lower than the recommended concentration (31.5 μM) of the World Health Organization (WHO) for copper ion. The binding mode of CMF and copper ions was studied through UV–visible spectroscopy, 1H NMR titration, ESI‐mass analysis, and DFT calculations. Sensing mechanism of CMF to Cu2+ was proposed to be the ligand‐to‐metal charge transfer (LMCT) through DFT calculations.
“…The chromone derivatives have been found to exhibit many interesting photoreactions like photodimerization, phototautomerization, photo‐oxidation, photorearrangements, photoreduction, and photoisomerization reactions. [ 35 ] Among these photoreactions, intramolecular hydrogen‐abstractions have been successfully utilized for the generations of some unique polyheterocyclic compounds. The exhilarated interest in the syntheses and photochemistry of variously substituted chromone systems has frequently enthralled the organic photochemists in the past decades.…”
The present research work describes the productive synthesis of novel bisbenzopyronopyran derivatives 4(a‐h) and 5(a‐h) via the photocyclization reactions of bischromones 3(a‐h) under the inert conditions. The latter compounds have been realized efficiently through the O‐alkylation reactions of the 3‐hydroxychromone 2 with suitable dihalogenated aliphatic/aromatic/heteroaromatic reagents in the presence of dry acetone/anhydrous K2CO3/Bu4N+I− (PTC). The cyclization reaction of chalcone 1 under the Algar‐Flynn‐Oyamada reaction conditions (KOH/H2O2) could results in the formation of compound 2 in the good yield. The structural scaffolds of the newly prepared bischromones and resultant bisbenzopyronopyrans have been certified from the meticulous analysis of their various spectroscopic parameters such as UV‐Vis, IR, 1H/13C‐NMR, and ESI‐MS. It was found that o/m/p‐xylene and pyridine‐linked final symmetrical bistetracycles exhibited higher antimicrobial potencies as compared to alkyl chain‐linked cyclized products. The bischromones 3(a‐h) could be able to endow modest level of antimicrobial behavior.
“…This approach has been extensively applied for the synthesis of novel heterocycles and in polymer chemistry. [4][5][6] Photodimerization is also frequently used for the dimerization of anthracenes, thiophenes, alkenes, five or sixmembered heterocycles, flavones, and chromones. [7][8][9] The presence of CQO and CQC chromophoric units in flavones as well as chromones makes them extremely active for photoreactions.…”
The irradiation of chromone-2-carboxylic esters with a blue LED in the presence of Rose Bengal and triethanolamine (TEOA) is used to obtain 2,2'-bichromanone of methyl, ethyl, n-propyl, iso-propyl, n-butyl, n-pentyl,...
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