Very efficient two-photon induced photo-tautomerization in non-symmetrical phthalocyanines

Drobizhev, Mikhail; Makarov, Nikolay S.; Rebane, Aleksander; Wolleb, Heinz; Spahni, Heinz

doi:10.1016/j.jlumin.2007.07.010

Cited by 12 publications

(9 citation statements)

References 14 publications

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“…Due to its structural flexibility, the synthesis and structure-property relationship of phthalocyanines continue attracting attention from the scientific community. For example, phthalocyanines with distinct ligands and central atoms have been used in various applications, such as the photovoltaic material in solar cells [8,9], all-optical switching [10], optical power limiting [11e13], molecular electronics [14,15], 3D optical data storage [16], sensors [17,18], electrochromic and photochromic systems [19,20] and photodynamic therapy [21e23], and so on.…”

Section: Introductionmentioning

confidence: 99%

Investigation of ground and excited state photophysical properties of gadolinium phthalocyanine

et al. 2014

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Section: Introductionmentioning

confidence: 99%

Investigation of ground and excited state photophysical properties of gadolinium phthalocyanine

et al. 2014

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“…[5][6][7][8] These molecules are very attractive for applications based on nonlinear absorption, such as optical power limiting, 9,10 high-density volumetric data storage, 11,12 and deep tissue photodynamic therapy. 13,14 We have recently studied the 2PA spectra of a series of symmetrically substituted Pcs, and found strong, gerade-gerade (g-g) 2PA transitions in the energy region between the Q-and B-bands.…”

Section: Introductionmentioning

confidence: 99%

Alternative selection rules for one- and two-photon transitions in tribenzotetraazachlorin: Quasi-centrosymmetrical π-conjugation pathway of formally non-centrosymmetrical molecule

Makarov

Drobizhev

Wicks

et al. 2013

The Journal of Chemical Physics

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We compare the two-photon absorption (2PA) spectra of non-centrosymmetrical metal-free tribenzotetraazachlorin (H 2 TBTAC) and analogous symmetrical tetra-tert-butyl-phthalocyanine (H 2 TtBuPc). Surprisingly, despite formal lack of center of inversion, the 2PA spectrum of H 2 TBTAC displays a two-photon allowed transition at 935 nm, similar to gerade-gerade (g-g) transitions observed in H 2 TtBuPc and in other symmetrical phthalocyanines. This transition is even better resolved in the singlet-singlet excited-state absorption spectrum. We tentatively explain the survival of the g-g transition in H 2 TBTAC by assuming that the main π -electron conjugation pathway in the tetraazasubstituted tetrapyrrole macrocycle bypasses the outer parts of the two oppositely located isoindole rings and thus renders the optically responsive core of the chromophore quasi-centrosymmetrical. By using the independently measured ground-and excited-state absorption extinction coefficients, we also show that the two-photon absorptivity can be quantitatively explained by a simple threelevel model with the lowest energy Q 1 state serving as an intermediate level.

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“…In contrast, only a few reports on two-photon induced photoconversions can be found. Härtner et al showed two-photon induced cycloreversion reactions of 7-hydroxycoumarin for drug delivery [1] , and the phototautomerisation of phthalocynanines was investigated by Dobrizhev et al [2] In a previous contribution [3] we reported on the synthesis and characterization of different polymers bearing phenyl ester units. Upon UV illumination, the photo-Fries reaction is observed in these polymers.…”

Section: Introductionmentioning

confidence: 99%

Index patterning of photoreactive polymers

et al. 2009

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Photoreactive polymeric materials have been investigated under one-photon (linear) and two photon (non linear) absorption conditions. A selected chromophore, 4-(N,N-diphenylamino)phenyl benzoate, was covalently attached to different polymer backbones (polystyrene, polynorbornene and polysiloxane). It is shown, that the predominant photoreaction of the chromophore is a photo-decarboxylation (extrusion of CO 2 ) both for two-photon and one-photon conditions. The large increase in refractive index, which results from this reaction, allows the optical patterning of the polymeric systems by conventional and two-photon radiation processes. The materials were investigated by ellipsometry, UV-VIS and FT-IR spectroscopy, FT-IR and phase contrast microscopy. Under two-photon conditions, threedimensional index structures were inscribed in the polymers, which can be used as optical waveguides.

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Very efficient two-photon induced photo-tautomerization in non-symmetrical phthalocyanines

Cited by 12 publications

References 14 publications

Investigation of ground and excited state photophysical properties of gadolinium phthalocyanine

Investigation of ground and excited state photophysical properties of gadolinium phthalocyanine

Alternative selection rules for one- and two-photon transitions in tribenzotetraazachlorin: Quasi-centrosymmetrical π-conjugation pathway of formally non-centrosymmetrical molecule

Index patterning of photoreactive polymers

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