Tripyrroledimethine-derived ("texaphyrin"-type) macrocycles: potential photosensitizers which absorb in the far-red spectral region

Jonathan L. Sessler; Gregory Hemmi; Bhaskar G. Maiya; Anthony Harriman; Millard M. Judy; Richard L. Boriak; James Lester Matthews; Benjamin Ehrenberg; Zvi Malik; Yeshayahu Nitzan; Angelika C. Rueck

doi:10.1117/12.44072

1 June 1991 Tripyrroledimethine-derived ("texaphyrin"-type) macrocycles: potential photosensitizers which absorb in the far-red spectral region

Jonathan L. Sessler, Gregory Hemmi, Bhaskar G. Maiya, Anthony Harriman, Millard M. Judy, Richard L. Boriak, James Lester Matthews, Benjamin Ehrenberg, Zvi Malik, Yeshayahu Nitzan, Angelika C. Rueck

Author Affiliations +

Proceedings Volume 1426, Optical Methods for Tumor Treatment and Early Diagnosis: Mechanisms and Techniques; (1991) https://doi.org/10.1117/12.44072
Event: Optics, Electro-Optics, and Laser Applications in Science and Engineering, 1991, Los Angeles, CA, United States

Abstract

The syntheses of three new cadmium(II)-containing tripyrroledimethine-derived, ''texaphyrin''-type, macrocycles, 14,15-dicyano-4,5,9,20-tetraethyl-10,19-dimethyl-13,16,21,22,23- pentazatetracyclo[16.2 .1.13,6.18,11]tricosa-1,3,5,7,9,11(23)12,14,16,18(21),19-undecaene (1), 4,5,9,28-tetraethyl-10,27-dimethyl-13,24,29,30,31- pentaazahexaacyclo$B24.2.1.13,6. 18,11.014,23.016,21]-hentriaconta-1,,5,7,9,11(31),12,14(23),15,17,19, 21,24,26(29),27-pentadecaene (2), and 4,5,9,32-tetraethyl-10,31-dimethyl-13,28,33,34,35- pentaazaheptacyclo$B28.2.1.13,6. 18,11.014,27.015,20.021,26]pentariconta-1,3,5,7,9,11(35),12,14( 27),15(20),16,18,21(26),22,24,28,30(33,31-heptadecaene (3), are discussed. These compounds, which contain extended (pi) -systems, possess strong, low-energy, Q-like absorption bands in the 650-900 nm spectral region, making them of possible interest in photodynamic applications. Time-resolved absorption and emission laser studies have been carried out and the fluorescence and triplet absorption spectra, excited state yields and lifetimes, O2-quenching rate constants, and quantum yields for formation of O2(1(Delta) g) measured and related to the structure of the macrocycle. The results of preliminary cell localization and in vitro photodynamic anti-viral, anti-bacterial, and anti-leukemic cell inactivation studies carried out with these and/or the parent (omicron) -phenylenediamine-derived parent texaphyrin system, 4, are also presented.

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Jonathan L. Sessler, Gregory Hemmi, Bhaskar G. Maiya, Anthony Harriman, Millard M. Judy, Richard L. Boriak, James Lester Matthews, Benjamin Ehrenberg, Zvi Malik, Yeshayahu Nitzan, and Angelika C. Rueck "Tripyrroledimethine-derived ("texaphyrin"-type) macrocycles: potential photosensitizers which absorb in the far-red spectral region", Proc. SPIE 1426, Optical Methods for Tumor Treatment and Early Diagnosis: Mechanisms and Techniques, (1 June 1991); https://doi.org/10.1117/12.44072

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