Bianthrone photophysics and photochemistry: solvent heavy-atom-induced triplet state formation

Nicodem, David E.; Cunha, Maria Fernanda V. da

doi:10.1016/s1010-6030(96)04618-7

Cited by 3 publications

(1 citation statement)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In contrast to these facts, the formation of 3a was evidently decreased under the triplet-sensitized conditions. The addition of tribromomethane, an accelerator for the intersystem-crossing from a singlet-excited state to a triplet-excited state, to the photoreaction media resulted in a significant increase in the formation of 2a and the decrease in the formation of 3a in an accelerator-concentration dependent way (see Figure ). These facts strongly suggest that the triplet-excited state of 1a is related to the formation of 2a and its singlet-excited state plays a role in the formation of 3a .…”

Section: Resultsmentioning

confidence: 99%

Novel Photodegradation of the Antifungal Antibiotic Pyrrolnitrin in Anhydrous and Aqueous Aprotic Solvents

et al. 2002

View full text Add to dashboard Cite

The UV irradiation of pyrrolnitrin (1a), which is an antibiotic clinically useful against dermatophytosis and possesses a unique 2-(pyrrol-3-yl)nitrobenzene moiety in the molecule, in an anhydrous aprotic solvent resulted in the exclusive formation of transient 7,4'-dichlorospiro[1,3-dihydrobenzo(c)isoxazole-3,3'-pyrrolin-2'-one] (2a) via the intramolecular oxidation of the juxtaposed pyrrole ring by the triplet-excited nitro group. The irradiation in an aqueous aprotic solvent, however, allowed the concurrent occurrence of intramolecular cyclization by the singlet-excited nitro group in 1a and the hydroxylation at the 2-position of the pyrrole ring by water to afford 3,7-dichloro-8-hydroxy-8,8a-dihydropyrrolo[2,3-b]indol-2-one (3a), accompanied by the formation of 2a. Elongation of the irradiation time in these photoreactions caused a rapid consumption of the products, 2a and 3a, to give undetermined polar polymeric products. The present results indicate that the photodegradation of 1a is significantly influenced by the presence of water in the reaction media and by the nature of its excited state. Thus, the loss of the antifungal activities by the photosensitive antibiotic 1a was chemically proved.

show abstract

Section: Resultsmentioning

confidence: 99%

Novel Photodegradation of the Antifungal Antibiotic Pyrrolnitrin in Anhydrous and Aqueous Aprotic Solvents

et al. 2002

View full text Add to dashboard Cite

show abstract

Stereochemistry of Bistricyclic Aromatic Enes and Related Polycyclic Systems

Biedermann

Agranat

2014

Topics in Current Chemistry

View full text Add to dashboard Cite

Bistricyclic aromatic enes (BAEs) and related polycyclic systems are a class of molecular materials that display a rich variety of conformations, dynamic stereochemistry and switchable chirality, color, and spectroscopic properties. This is due to the a subtle interplay of the inherent preference for planarity of aromatic systems and the competing necessity of non-planarity due to intramolecular overcrowding in the fjord regions built into the general molecular structure of BAEs. The conformational, dynamic, and spectroscopic properties may be designed and fine-tuned, e.g., by variation of the bridging groups X and Y, the overcrowding in the fjord regions, extensions of the aromatic system, or other modifications of the general BAE structure, based on the fundamental understanding of the structure-property relationships (SPR). The present review provides an analysis of the conformational spaces and the dynamic stereochemistry of overcrowded bistricyclic aromatic enes applying fundamental symmetry considerations. The symmetry analysis presented here allows deeper insight into the conformations, chirality, and the mechanisms of the dynamic stereochemistry, and will be instrumental in future computational studies.

show abstract

Twisted diphenoquinones fused with thiophene rings: thiophene analogs of bianthrone

Adachi,

Hattori,

Mikie

et al. 2024

Chem. Commun.

View full text Add to dashboard Cite

show abstract

Bianthrone photophysics and photochemistry: solvent heavy-atom-induced triplet state formation

Cited by 3 publications

References 17 publications

Novel Photodegradation of the Antifungal Antibiotic Pyrrolnitrin in Anhydrous and Aqueous Aprotic Solvents

Novel Photodegradation of the Antifungal Antibiotic Pyrrolnitrin in Anhydrous and Aqueous Aprotic Solvents

Stereochemistry of Bistricyclic Aromatic Enes and Related Polycyclic Systems

Twisted diphenoquinones fused with thiophene rings: thiophene analogs of bianthrone

Contact Info

Product

Resources

About