Naphthalocyanine Derivatives Research Articles

Fiber Optic Probe Applications Using Near-Infrared Compounds: Determination of NaOH

Abstract The development of a near-infrared fiber optic probe (FOPP) for the determination of caustic soda will be reported. The utility of the FOPP is demonstrated using an NIR non-commercially available tetrasubstituted chloroaluminum naphthalocyanine NIR dye which is susceptible to pH changes in solutions. The naphthalocyanine derivatives have been synthesized in our laboratories. The spectral characteristics of these NIR dyes, are above 700 nm and the absorbance maximum is a perfect match for the use of semiconductor laser diodes as the excitation source. The response of the Q-band against solution pHs and caustic soda will be reported. The FOPP consists of a semiconductor laser diode (λmax=780 nm), an NIR dye and a detector. The probe made of poly(methyl methacrylate) serves as a support for a permeable polymer that is used for the entrapment of the NIR dye (about < 2mm in diameter). The permeable polymers used were Nafion and Gelatin. As hydrogen ions diffuse through the permeable polymer, a complex is formed with the dye, accompanied by changes in the spectral characteristics of the dye. Excitation of the complex is induced with a semiconductor laser diode at 780 nm. The probe shows good reproducibility of the data in NaOH measurements. Also the molar absorption coefficient of these dyes at different concentrations of polymer will be reported. The effect of Nafion on the spectral characteristics of the NIR dyes will be presented. The general procedure used for the attachment of the dye to the distal end of the probe can be used to construct compact non-invasive detectors. The use of photodiodes as detertors will be discussed. Use of smaller components shown here will allow for the manufacturing of portable instruments for applications in medicine and industry.

Unique molecular aggregation of novel naphthalocyanine (near IR absorbing dye)

A series of organic-soluble naphthalocyanine derivatives (Y m MNcX 4) have been synthesized. Their spectroscopic properties in organic solutions and in thin films were studied. MNcX 4 such as MNc(t-Bu) 4 ( 5a-5c) and MNc(On-Bu) 4 ( 5j) formed H-aggregates even in dilute solutions. MNc(CO 2R') 4 ( 5d-5i) had much stronger H-aggregation properties compared with those ofMNc(t-Bu) 4 and MNc(On-Bu) 4. Especially, MNc(CO 2R') 7 complexes (M=Cu, Pd and Ni) existed exclusively without monomers in the aggregated state even in highly dilute solutions. MNcX 4, which has strong H-aggregation properties, showed merely H- aggregate absorption maxima in thin films. In contrast, Y 2MNcX 4 ( 4), which has sterically hindered Y groups, showed monomerically pure characteristics in solution. However, thin films of Y 2MNcX 4 have a J-type molecular arrangement, exhibiting a red shift of Q-band absorption. The monomeric properties of Y 2MNcX 4 in solutions and J-type molecular arrangement in thin films arise from steric hindrance of two Y groups, such as R 3SiO-in Y 2MNcX 4, which prevents strong H-aggregation of naphthalocyanine.

Photoelectrochemical Investigations on Naphthalocyanine Derivatives in Thin Films

Photoelectrochemical properties of Zn-naphthalocyanine (ZnNc) and its modified compound, Zn-2,3-tetraquinoxalinotetraazaporphyrin (ZnTQP) were investigated in thin films. The ZnNc electrode vacuum-deposited on an indium tin oxide (ITO) substrate exhibited almost an ohmic I-V curve in the dark and small cathodic photocurrents under illumination, which was typical for the p-type semiconduction of the ZnNc layer, in a photoelectrochemical cell. The drop-casted film electrode of ZnTQP, on the other hand, showed rectified I-V characteristics in the dark and high anodic photocurrents under illumination, which was attributed to the n-type semiconducting character of the ZnTQP layer. These different photoelectrochemical behaviors were characterized by photocurrent action spectra and ultraviolet photoelectron spectroscopy. The substitution with quinoxalino groups into the Nc macrocyclic system gave rise to lowering of the HOMO energy level for the TQP molecule. This electronic energy shift generated donor electron states in the band gap after contact with the substrate or electrolyte and enabled the photooxidation at the valence band edges corresponding to the Soret-and Q-band excitations. 55 refs., 10 figs.

Pharmacokinetic and tissue distribution studies of the photosensitizer bis(di-isobutyl octadecylsiloxy)silicon 2,3-naphthalocyanine (isoBOSINC) in normal and tumor-bearing rats.

Bis(di-isobutyl octadecylsiloxy)silicon 2,3-naphthalocyanine (isoBOSINC) is a representative of a group of naphthalocyanine derivatives with spectral and photophysical properties that make them attractive candidates for photodynamic therapy (PDT). Tissue distributions were studied in normal and in tumor-bearing rats as a function of time following intravenous injection of isoBOSINC as a suspension in 10% Tween 80 in saline. The dose studied was 0.25 mg/kg of body weight. The compound isoBOSINC was isolated from several tissues and organs, as well as tumors and peritumoral muscles and skin, and quantitated by a high-performance liquid chromatographic technique. The tumor model, an N-(4-[5-nitro-2-furyl]-2-thiazolyl)formamide (FANFT)-induced urothelial cell carcinoma, was transplanted into the hind legs of Fischer 344 rats. The dye was retained in tumors at higher concentrations than in all tissues and organs examined, except for spleen and liver. The highest concentration ratio of dye in tumor versus peritumoral muscle (24.5) occurred 9 h after injection. Serum clearance of isoBOSINC showed similar kinetic behavior for both groups of rats, with a t 1/2 of elimination of approximately 10 h. At 7 and 14 days postinjection, the levels of dye found in testes were generally higher than in most other tissues, except spleen and liver. Concentrations of isoBOSINC were either very low or not detectable in rat brain. Trace amounts of the dye were excreted in the urine, and by day 14 approximately 17% of the dose was accounted for in the feces. The significant levels of the drug in tumors, as well as the excellent ratios of tumor-to-muscle concentration observed, have promising implications for PDT of tumors.

Third-order nonlinear optical properties of a vanadyl naphthalocyanine derivative

Third-order nonlinear optical susceptibility of a vanadylnaphthalocyanine (VONc) possessing terminal tetrakis(pentoxycarbonyl) (COO-C 5 H 11 ) substituents is reported for the first time. The χ (3) (-3ω; ω, ω, ω) values measured by the third harmonic generation technique between 2.1 and 1.5 μm varied with the wavelengths, increasing closer to resonance. The maximum χ (3) (-3ω; ω, ω, ω) determined for VONc(COO-C 5 H 11 ) 4 was 8.6×10 -11 esu at 2.1 μm

Octa-alkoxy phthalocyanine and naphthalocyanine derivatives: dyes with Q-band absorption in the far red or near infrared

Download options Please wait... Article information DOI https://doi.org/10.1039/P19880002453 Article type Paper Download Citation J. Chem. Soc., Perkin Trans. 1, 1988, 2453-2458 BibTex EndNote MEDLINE ProCite ReferenceManager RefWorks RIS Permissions Request permissions Octa-alkoxy phthalocyanine and naphthalocyanine derivatives: dyes with Q-band absorption in the far red or near infrared M. J. Cook, A. J. Dunn, S. D. Howe, A. J. Thomson and K. J. Harrison, J. Chem. Soc., Perkin Trans. 1, 1988, 2453 DOI: 10.1039/P19880002453 To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page. If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given. If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page. Read more about how to correctly acknowledge RSC content. Search articles by author Michael J. Cook Adrian J. Dunn Steven D. Howe Andrew J. Thomson Kenneth J. Harrison