Strong two-photon absorption in new porphyrins with asymmetrical <i>meso</i>-substitution

Mikhail Drobizhev; Aliaksandr Karotki; Mikalai Kruk; Yuliya Dzenis; Aleksander Rebane; Fanqing Meng; Eric Nickel; Charles W. Spangler

doi:10.1117/12.505849

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3 November 2003 Strong two-photon absorption in new porphyrins with asymmetrical meso-substitution

Mikhail Drobizhev, Aliaksandr Karotki, Mikalai Kruk, Yuliya Dzenis, Aleksander Rebane, Fanqing Meng, Eric Nickel, Charles W. Spangler

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Proceedings Volume 5211, Nonlinear Optical Transmission and Multiphoton Processes in Organics; (2003) https://doi.org/10.1117/12.505849
Event: Optical Science and Technology, SPIE's 48th Annual Meeting, 2003, San Diego, California, United States

Abstract

Porphyrins and related molecules with strong two-photon absorption (TPA) are extremely called for because of several emerging applications, including 3D optical memory, high-resolution fluorescence microscopy and photodynamic therapy. In this paper we demonstrate for the first time that an asymmetric meso-substitution of porphyrin macrocycle with electron-donating diphenylamino-stilbene or bis-(diphenylamino)-stilbene groups results in a drastic enhancement of intrinsic TPA cross section in the near-IR region. The cross section value amounts to 500 - 900 GM depending on substituent group and link structure, which is about 10² times the corresponding value for the unsubstituted parent molecule. Compared to symmetrical porphyrins, the TPA spectra of this series follow qualitatively the corresponding one-photon spectra. Therefore, we describe the observed TPA spectra and absolute cross section values by taking into account the change of permanent dipole moment upon excitation. A new zeroth-generation dendrimer, consisting of a porphyrin core, symmetrically tertakis-meso-substituted with strong TPA dendrons, reveals 7 times increase of the cross section (740 vs 110 GM) as compared to its mono-meso-substituted analogue. We also demonstrated an efficient singlet oxygen generation upon two-photon excitation of these new molecules, which makes them particularly attractive for photodynamic therapy.

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Mikhail Drobizhev, Aliaksandr Karotki, Mikalai Kruk, Yuliya Dzenis, Aleksander Rebane, Fanqing Meng, Eric Nickel, and Charles W. Spangler "Strong two-photon absorption in new porphyrins with asymmetrical meso-substitution", Proc. SPIE 5211, Nonlinear Optical Transmission and Multiphoton Processes in Organics, (3 November 2003); https://doi.org/10.1117/12.505849

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