Water-soluble sulfonated phosphorus(v) corrolazines and porphyrazines: the effect of macrocycle contraction and pyrazine ring fusion on spectral, acid-base and photophysical properties

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F22%3A00550871" target="_blank" >RIV/61388955:_____/22:00550871 - isvavai.cz</a>

Alternative codes found

RIV/00216208:11160/22:10450587

Result on the web

<a href="http://hdl.handle.net/11104/0326178" target="_blank" >http://hdl.handle.net/11104/0326178</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d1dt02453a" target="_blank" >10.1039/d1dt02453a</a>

Result language

angličtina

Original language name

Water-soluble sulfonated phosphorus(v) corrolazines and porphyrazines: the effect of macrocycle contraction and pyrazine ring fusion on spectral, acid-base and photophysical properties

Original language description

Novel water-soluble dihydroxophosphorus(v) complexes of sulphophenyl substituted porphyrazine (6), corrolazine (7) and its pyrazine fused derivative (8) were prepared and their spectral, acid-base and photophysical properties in aqueous solutions were studied. Due to the presence of eight SO3H groups, the compounds were fully monomeric (7 and 8) or only slightly aggregated (6) in water. Spectrophotometric titration revealed that the two stage deprotonation of axially bonded hydroxy groups can be achieved for porphyrazine 6 (pK(a1) = 5.62, pK(a2) = 9.13) and pyrazine fused corrolazine 8 (pK(a1) = 6.5, pK(a2) = 11.7), while only the first dissociation stage could be observed for corrolazine 7 (pK(a1) = 9.94). The fluorescence emission of the corrolazines 7, 8 and especially porphyrazine 6 was low in water (Phi(F) = 0.086, 0.18, and 0.014, respectively) and completely quenched under basic conditions due to photoinduced electron transfer. In comparison with porphyrazine 6, the contraction of the macrocycle in the corrolazines 7 and 8 induced significant improvement of singlet oxygen production in water reaching values of Phi(Delta) = 0.56 and 0.43, respectively, which makes the corrolazines promising photosensitizers for photodynamic therapy. The observed evolution of the electronic absorption spectra and fluorescence quenching observed in a basic medium was explained using the model DFT calculations (cc-pvtz basis set) performed for the dihydroxophosphorus(v) complexes of unsubstituted porphyrazine and corrolazine and their mono- and doubly deprotonated forms.

Czech name

—

Czech description

—

Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10403 - Physical chemistry

Project

—

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2022

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Dalton Transactions

ISSN

1477-9226

e-ISSN

1477-9234

Volume of the periodical

51

Issue of the periodical within the volume

4

Country of publishing house

GB - UNITED KINGDOM

Number of pages

14

Pages from-to

1364-1377

UT code for WoS article

000732842800001

EID of the result in the Scopus database

2-s2.0-85123799707