Triphenylmethanol
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Triphenylmethanol

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Triphenylmethanol (Zidovudine EP Impurity D) is a triaryl methane derivative as antiproliferative agent.

Category
Others
Catalog number
BAT-008045
CAS number
76-84-6
Molecular Formula
C19H16O
Molecular Weight
260.33
Triphenylmethanol
IUPAC Name
triphenylmethanol
Synonyms
triphenylmethanol
Appearance
White to off-white solid
Purity
≥ 99 % (HPLC)
Density
1.13 g/cm3
Melting Point
159-164 ℃
Boiling Point
380.0 ℃ at 760 mmHg
Storage
Store at RT
Solubility
Soluble in Chloroform, DMSO, Ethyl Acetate, Methanol
InChI
InChI=1S/C19H16O/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,20H
InChI Key
LZTRCELOJRDYMQ-UHFFFAOYSA-N
Canonical SMILES
C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)O
1. Photoactivatable aggregation-induced emission of triphenylmethanol
Yue Zheng, Xiaokun Zheng, Yu Xiang, Aijun Tong Chem Commun (Camb). 2017 Oct 10;53(81):11130-11133. doi: 10.1039/c7cc04693f.
Triphenylmethanol (TPOH) is a non-fluorescent compound. Interestingly, after UV irradiation at 254 nm, TPOH showed a strong blue fluorescence on a solid surface. Moreover, the fluorescence can be quenched by UV irradiation at 365 nm, making the photoactivatable fluorescence reversible. TPOH is thus applied for rewritable photopatterning tuned by UV light.
2. Deciphering the hydrogen-bonding scheme in the crystal structure of triphenylmethanol: a tribute to George Ferguson and co-workers
Tomasa Rodríguez Tzompantzi, Aldo Guillermo Amaro Hernández, Rosa Luisa Meza-León, Sylvain Bernès Acta Crystallogr C Struct Chem. 2019 Sep 1;75(Pt 9):1266-1273. doi: 10.1107/S2053229619010714. Epub 2019 Aug 14.
The crystal structure of triphenylmethanol, C19H16O, has been redetermined using data collected at 295 and 153 K, and is compared to the model published by Ferguson et al. over 25 years ago [Ferguson et al. (1992). Acta Cryst. C48, 1272-1275] and that published by Serrano-González et al., using neutron and X-ray diffraction data [Serrano-González et al. (1999). J. Phys. Chem. B, 103, 6215-6223]. As predicted by these authors, the hydroxy groups are involved in weak intermolecular hydrogen bonds in the crystal, forming tetrahedral tetramers based on the two independent molecules in the asymmetric unit, one of which is placed on the threefold symmetry axis of the R-3 space group. However, the reliable determination of the hydroxy H-atom positions is difficult to achieve, for two reasons. Firstly, a positional disorder affects the full asymmetric unit, which is split over two sets of positions, with occupancy factors of ca 0.74 and 0.26. Secondly, all hydroxy H atoms are further disordered, either by symmetry, or through a positional disorder in the case of parts placed in general positions. We show that the correct description of the hydrogen-bonding scheme is possible only if diffraction data are collected at low temperature. The prochiral character of the hydrogen-bonded tetrameric supramolecular clusters leads to enantiomorphic three-dimensional graphs in each tetramer. The crystal is thus a racemic mixture of supS and supR motifs, consistent with the centrosymmetric nature of the R-3 space group.
3. Triphenylmethanol-triphenylphosphine oxide (1/1)
T Steiner Acta Crystallogr C. 2000 Aug;56 (Pt 8):1033-4. doi: 10.1107/s0108270100007423.
In the crystalline 1:1 molecular complex of triphenylmethanol (TPMeOH) and triphenylphosphine oxide (TPPO), C(19)H(16)O. C(18)H(15)OP, molecular dimers are formed which are linked by O-H. O=P hydrogen bonds. The dimers are aligned by sixfold phenyl embraces to form columns. The structure is disordered with half a dimer per asymmetric crystal unit, i.e. with only one molecular site which is half-occupied by both TPMeOH and TPPO.
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