Synthesis of Heteroatom Substituted Naphthoporphyrazine Derivatives with Near-Infrared Absorption and Emission

Abstract

In an effort to develop effective new optical contrast agents, we report the synthesis of porphyrazines (pzs) of the form H(2)[pz(A(4-n);C(n))], n = 1, and 2 (trans-), where "A" represents peripheral heteroatom (S- and O-) R-groups and "C" is a fused, beta,beta'-diisopropyloxynaphtho group. The sulfide appended trans-H(2)[pz(A(2);C(2))] pz (7) has the longest wavelength absorption, approximately 874 nm (log epsilon = 4.53), and S(1) fluorescence at approximately 927 nm, wavelengths within the window of maximum tissue penetration. Emission from the oxygen-atom appended naphtho-pzs (8, 9) has been observed within carcinoma cells, confirming cellular uptake and their potential use as optical agents.

Water soluble quarternizable gallium and indium phthalocyanines bearing quinoline 5-sulfonic acid: Synthesis, aggregation, photophysical and electrochemical studies

“…R and R Std are the DPBF (or ADMA) photobleaching rates in the presence of the respective samples (3,4,5,6) and standard, respectively. I abs and I Std abs are the rates of light absorption by the samples (3,4,5,6) and standard, respectively.…”

“…R and R Std are the DPBF (or ADMA) photobleaching rates in the presence of the respective samples (3,4,5,6) and standard, respectively. I abs and I Std abs are the rates of light absorption by the samples (3,4,5,6) and standard, respectively. To avoid chain reactions induced by DPBF (or ADMA) in the presence of singlet oxygen [39], the concentration of quencher (DPBF or ADMA) was lowered to $3 Â 10 À5 mol dm À3 solutions of sensitizer (containing DPBF or ADMA)) were prepared in the dark and irradiated in the Q band region using the setup described above.…”

“…where C 0 and C t are the sample (3, 4, 5, 6) concentrations before and after irradiation respectively, V is the reaction volume, N A the Avogadro's constant, S the irradiated cell area and t the irradiation time, I abs is the overlap integral of the radiation source light intensity and the absorption of the samples (3,4,5,6). A light intensity of 2.50 Â 10 16 photons s À1 cm À2 was employed for F d determinations.…”

“…Metal phthalocyanine (MPc) is a kind of promising complex which has high technological application fields with various metal ions in its central cavity [1][2][3]. In recent years, many efforts to make the best specified molecular materials aredevoted on chemical sensors [4][5][6], semiconductors [7], electrochromic display devices [8][9][10], liquid crystals [11,12], solar cells [13], photovoltaics [14] various catalytic processes [15,16] and photosensitizers [17,18].…”

“…Their redox behaviour was measured by voltammetry and in situ spectroelectrochemistry. The nature of the substituent and solvent effect on the photophysical and photochemical parameters of the substituted phthalocyanines (3,4,5,6) are also reported. The effect of binding position on the electrochemical properties of newly synthesized phthalocyanine compounds, periphery (b-) and non-periphery (a-) substituted with 8-hydroxyquinoline-5-sulfonic acid group were evaluated.…”