1283004-75-0Relevant academic research and scientific papers
In vitro investigation of the antimicrobial activity of a series of lipophilic phenols and naphthols
Govender, Thavendran,Govinden, Usha,Mocktar, Chunderika,Kruger, Hendrik G.,Veljkovi?, Jelena,Cindro, Nikola,Bobinac, Damir,?ab?i?, Ivana,Mlinari?-Majerski, Kata,Basari?, Nikola
, p. 44 - 50 (2016/03/30)
Five groups of phenols/naphthols (42 compounds in total) were synthesized and screened against Gram-positive Staphylococcus aureus and Bacillus subtilis, Gram-negative Escherichia coli and Klebsiella pneumoniae, and the fungus Candida albicans. Whereas co
Competing photodehydration and excited-state intramolecular proton transfer (ESIPT)in adamantyl derivatives of 2-phenylphenols
Basaric, Nikola,Cindro, Nikola,Hou, Yunyan,Zabcic, Ivana,Mlinaric-Majerski, Kata,Wan, Peter
, p. 221 - 234 (2011/04/23)
2-Phenylphenol derivatives strategically substituted with a hydroxyadamantyl substituent were synthesized and their photochemical reactivity was investigated. Derivatives 9 and 10 undergo competitive excited-state intramolecular proton transfer (ESIPT) from the phenol to the carbon atom of the adjacent phenyl ring and formal ESPT from the phenol to the hydroxyl group coupled with dehydration. These two processes (both via S1) give rise to two classes of quinone methides (QMs) that revert to starting material or react with nucleophiles, respectively. ESIPT to carbon atoms was studied by performing photolysesin the presence of D2O, whereupon deuterium incorporation to the adjacent phenyl ring was observed (Φ = 0.1-0.2). The competing formal ESPT and dehydration takes place with quantum yields that are an order of magnitude lower and was studied by isolation of photomethanolysis products. Derivative 8 did not undergo ESIPT to carbon atom. Owing to the presence of an intramolecular H bond, an efficient ESIPT from the phenol to the hydroxyl group coupled with dehydration gives a QM that efficiently undergoes electrocyclization (overall Φ = 0.33), to give chroman 16. In addition, spiro[adamantane-2,9′-(4′-hydroxy)fluorene] (12) undergoes ESIPT, unlike the previously reported unreactive parent 2-hydroxyfluorene. The reactive singlet excited states of the prepared biphenyl and fluorene molecules were characterized by fluorescence spectroscopy, whereas laser flash photolysis (LFP) was performed to characterize the longer lived QM intermediates.
