7465-58-9Relevant academic research and scientific papers
Strong intramolecular hydrogen bonding and molecular vibrations of 9-hydroxyphenalen-1-one
Kovacs, Attila,Izvekov, Vladislav,Zauer, Karoly,Ohta, Koji
, p. 5000 - 5009 (2001)
The strong intramolecular hydrogen bonding in 9-hydroxyphenalen-1-one (1) has been investigated by means of quantum chemical calculations and vibrational spectroscopy. Both ab initio molecular orbital (MP2) and density functional theory (B3-LYP, B3-P86) calculations predict a double-minimum potential energy surface with a low (ca. 10 kJ/mol) barrier. The hydrogen-bonding energy, estimated by comparison with the non-hydrogen-bonded anti conformer, is ca. 60 kJ/mol. Our comparative study of the three theoretical levels revealed the very good performance of the B3-LYP density functional in conjunction with a diffuse polarized valence triple-ζ basis set, while the B3-P86 functional tends to overestimate considerably the strong hydrogen-bonding interaction. Based on a joint analysis of the energetics and molecular geometry, the interaction in 1 can be classified as a border case between traditional and short-strong hydrogen bonds. The charge distribution refers to a strong ionic character of the hydrogen-bonding interaction. The vibrational properties of the molecule have been investigated by a combined experimental (FT-IR, FT-Raman) and theoretical analysis. The deficiencies of the computed harmonic force field were corrected by the scaled quantum mechanical (SQM) method of Pulay et al. As a result of our SQM analysis, 45 from a total of 63 fundamentals of the molecule were assigned with an rms deviation of 6.9 cm-1 between the experimental and scaled frequencies. The most characteristic effect of hydrogen bonding on the vibrational properties of 1 is the enhanced mixing of the CO and OH vibrations with each other and with the skeletal modes.
Exceptional oxygen sensing properties of new blue light-excitable highly luminescent europium(III) and gadolinium(III) complexes
Borisov, Sergey M.,Fischer, Roland,Saf, Robert,Klimant, Ingo
, p. 6548 - 6560 (2014)
New europium(III) and gadolinium(III) complexes bearing 8-hydroxyphenalenone antenna combine efficient absorption in the blue part of the spectrum and strong emission in polymers at room temperature. The Eu(III) complexes show characteristic red luminescence whereas the Gd(III) dyes are strongly phosphorescent. The luminescence quantum yields are about 20% for the Eu(III) complexes and 50% for the Gd(III) dyes. In contrast to most state-of-the-art Eu(III) complexes the new dyes are quenched very efficiently by molecular oxygen. The luminescence decay times of the Gd(III) complexes exceed 1 ms which ensures exceptional sensitivity even in polymers of moderate oxygen permeability. These sensors are particularly suitable for trace oxygen sensing and may be good substitutes for Pd(II) porphyrins. The photophysical and sensing properties can be tuned by varying the nature of the fourth ligand. The narrow-band emission of the Eu(III) allows efficient elimination of the background light and autofluorescence and is also very attractive for use e.g., in multi-analyte sensors. The highly photostable indicators incorporated in nanoparticles are promising for imaging applications. Due to the straightforward preparation and low cost of starting materials the new dyes represent a promising alternative to the state-of-the-art oxygen indicators particularly for such applications as, e.g., food packaging.
A Green-Absorbing, Red-Fluorescent Phenalenone-Based Photosensitizer as a Theranostic Agent for Photodynamic Therapy
Kaye, Esther G.,Kailass, Karishma,Sadovski, Oleg,Beharry, Andrew A.
supporting information, p. 1295 - 1301 (2021/08/01)
Phenalenone is a synthetically accessible, highly efficient photosensitizer with a near-unity singlet oxygen quantum yield. Unfortunately, its UV absorption and lack of fluorescence has made it unsuitable for fluorescence-guided photodynamic therapy against cancer. In this work, we synthesized a series of phenalenone derivatives containing electron-donating groups to red-shift the absorption spectrum and bromine(s) to permit good singlet oxygen production via the heavy-atom effect. Of the derivatives synthesized, the phenalenone containing an amine at the 6-position with bromines at the 2- and 5-positions (OE19) exhibited the longest absorption wavelength (i.e., green) and produced both singlet oxygen and red fluorescence efficiently. OE19 induced photocytotoxicity with nanomolar potency in 2D cultured PANC-1 cancer cells as well as light-induced destruction of PANC-1 spheroids with minimal dark toxicity. Overall, OE19 opens up the possibility of employing phenalenone-based photosensitizers as theranostic agents for photodynamic cancer therapy.
Ligand mixed-valence and electrical conductivity in coordination complexes containing a redox-active phenalenol-substituted ligand
Dale, Sarah,Bonanno, Nico M.,Pelaccia, Mark,Lough, Alan J.,Miyawaki, Atsuhiro,Takahashi, Kazuyuki,Lemaire, Martin T.
supporting information, p. 8053 - 8056 (2019/06/18)
A new redox-active hydrazone ligand bearing a phenalenol group is described (phpl), which produces neutral six-coordinate Fe and Co complexes (1 & 2) with the ligands identified in different oxidation states; an open-shell anion radical and closed-shell dianion. An intense and very low-energy intervalence charge transfer (IVCT) band is identified in solid-state and in solution in the complexes. Single crystals of 1 are semiconducting (at 300 K, σ = 3.05 × 10-4 S cm-1 with Ea = 245 meV).
A safe and efficacious Pt(ii) anticancer prodrug: Design, synthesis,: In vitro efficacy, the role of carrier ligands and in vivo tumour growth inhibition
Dutta, Pradip Kumar,Sharma, Rupali,Kumari, Smita,Dubey, Ravindra Dhar,Sarkar, Sujit,Paulraj, Justin,Vijaykumar, Gonela,Pandey, Manoj,Sravanti,Samarla, Mallik,Das, Hari Sankar,Yashpal,Heeralal,Goyal, Ravinder,Gupta, Nimish,Mandal, Swadhin K.,Sengupta, Aniruddha,Sarkar, Arindam
supporting information, p. 1718 - 1721 (2019/02/12)
Diaminocyclohexane-Pt(ii)-phenalenyl complexes (1 and 2) showed an appropriate balance between efficacy and toxicity. Compound 2 showed nearly two-fold higher tumour growth inhibition than oxaliplatin in a murine NSCLC tumour model, when a combined drug development approach was used. The fluorescent properties of phenalenone were utilized to understand the mechanistic details of the drug.
FLUORESCENT ANTICANCER PLATINUM DRUGS
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Paragraph 0388, (2018/11/21)
The present disclosure is in relation to the field of nanotechnology and cancer therapeutics. In particular, the present disclosure relates to fluorescent platinum based compounds. The disclosure further relates to synthesis of said fluorescent platinum based compounds, nanoparticles and compositions comprising said fluorescent platinum based compounds/nanoparticles. The disclosure also relates to methods of managing cancer by the fluorescence changes between aforesaid platinum based compounds and corresponding free ligands, nanoparticles and compositions.
Europium (III) complex functionalized Si-MCM-41 hybrid materials with visible-light-excited luminescence
Gu, Yan-Jing,Yan, Bing
, p. 96 - 102 (2013/10/22)
The synthesis of organics 9-hydroxyphenalenone (HPO), 2-methyl-9- hydroxyphenalenone (MHPO), 6-hydroxybenz[de]anthracen-7-one (HBAO), 5-amino-1,10-phenanthroline (phen-NH2) and its functionalized mesoporous MCM-41 by covalent band are reported, as well as those of Europium (III) hybrid mesoporous materials, EuL3phen-MCM-41 (L = HPO, MHPO, HBAO). The photoluminescence and microstructural properties are characterized, and the XRD and BET results revealed that all of these hybrid materials have uniformity in the mesostructure. It is worth noting that the excitation spectra of these hybrid materials have a broad absorption, which occupies from UV to visible region (250-475 nm). Upon ligand-mediated excitation with the visible light, the low efficient energy transfer exhibit between the organic ligands and europium(III) ion under visible excitation, but the maximum wavelength (456 nm/457 nm/451 nm) located at blue light region, which is in consistent with the blue LED light, then might be a feasible alternative in producing time-resolved luminescence under LED-excitation.
PREPARATION, PROPERTIES, AND SOME CHEMICAL REACTIONS OF PHENALENOFURAN
Weeratunga, Gamini,Austrup, Mona,Rodrigo, Russell
, p. 3169 - 3174 (2007/10/02)
The synthesis of hitherto unknown phenalenofuran (1), in 11 percent overall yield from 2-naphthol, has been achieved.Its (1)H and (13)C n.m.r. spectra have been fully assigned by means of heteronuclear 2D correlations.The furanoid moiety of (1) displays Diels-Alder diene reactivity in its reactions with benzyne, dimethyl acetylenedicarboxylate, and singlet oxygen.The furan ring of (1) also suffers oxidation by m-chloroperbenzoic acid and undergoes catalytic hydrogenation.This chemistry appears to be more characteristic of naphthofuran than of naphthofuran although both structural units co-exist in structure (1).
