TY - JOUR
T1 - Phosphorus(V)-corrole
T2 - Synthesis, spectroscopic properties, theoretical calculations, and potential utility for in vivo applications in living cells
AU - Liang, Xu
AU - Mack, John
AU - Zheng, Li Min
AU - Shen, Zhen
AU - Kobayashi, Nagao
PY - 2014/3/17
Y1 - 2014/3/17
N2 - The synthesis and properties of phosphorus(V) 5,10,15-tris(4- methoxycarbonylphenyl)corrole (1) have been investigated, and its potential utility for bioimaging applications in living cells has been explored. As would normally be anticipated for corrole complexes, the intensity of the Q(0,0) bands of 1 is greater than those of comparable phosphorus(V) tetraphenylporphyrins, but the ΦF values (0.25 for 1) are found to be comparable. A detailed analysis of the electronic structure of the complex was carried out by comparing electronic absorption and MCD spectral data to the results of TD-DFT calculations. The meso-aryl substituents, which enhance the lipophilicity of 1 and hence result in its localization in intracellular membranes during HeLa cell experiments, are predicted to result in a narrowing of the HOMO-LUMO gap and hence a red shift of the Q(0,0) bands toward the optical window in biological tissues.
AB - The synthesis and properties of phosphorus(V) 5,10,15-tris(4- methoxycarbonylphenyl)corrole (1) have been investigated, and its potential utility for bioimaging applications in living cells has been explored. As would normally be anticipated for corrole complexes, the intensity of the Q(0,0) bands of 1 is greater than those of comparable phosphorus(V) tetraphenylporphyrins, but the ΦF values (0.25 for 1) are found to be comparable. A detailed analysis of the electronic structure of the complex was carried out by comparing electronic absorption and MCD spectral data to the results of TD-DFT calculations. The meso-aryl substituents, which enhance the lipophilicity of 1 and hence result in its localization in intracellular membranes during HeLa cell experiments, are predicted to result in a narrowing of the HOMO-LUMO gap and hence a red shift of the Q(0,0) bands toward the optical window in biological tissues.
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U2 - 10.1021/ic402347w
DO - 10.1021/ic402347w
M3 - Article
C2 - 24597460
AN - SCOPUS:84896365532
VL - 53
SP - 2797
EP - 2802
JO - Inorganic Chemistry
JF - Inorganic Chemistry
SN - 0020-1669
IS - 6
ER -