Singlet-Oxygen-Sensitized Delayed Fluorescence:  Direct Detection of Triplet Phthalocyanine as an Intermediate

Murphy, Sean T.; Kondo, and Kunio; Foote, Christopher S.

doi:10.1021/ja974293g

Cited by 30 publications

(14 citation statements)

References 27 publications

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“…Thermally-activated endoperoxide chemiluminescence26, 27, 28 and the related phenomenon of singlet oxygen sensitized fluorescence29, 30, 31, 32, 33 have been investigated for more than three decades and the substantial body of published work provides an excellent knowledge base for our ongoing mechanistic studies. It is also worth noting that squaraines are efficient acceptors of singlet oxygen energy 12.…”

Section: Resultsmentioning

confidence: 99%

Storable, thermally activated, near-infrared chemiluminescent dyes and dye-stained microparticles for optical imaging

et al. 2010

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Optical molecular imaging employs relatively harmless, low-energy light and technically straightforward instrumentation. Self-illuminating, chemiluminescent systems are especially attractive since they have inherently high signal contrast due to the lack of background emission. Currently, chemiluminescence imaging involves short-lived molecular species that are not stored but instead generated in situ, and they typically emit visible light, which does not penetrate far through heterogeneous biological media. Here, we describe a new paradigm for optical molecular imaging using squaraine rotaxane endoperoxides (SREPs), interlocked fluorescent and chemiluminescent dye molecules that have a squaraine chromophore encapsulated inside a macrocycle endoperoxide. SREPs can be stored indefinitely at temperatures below −20 °C, but upon warming to body temperature they undergo a unimolecular chemical reaction and emit near infrared light that can pass through a living mouse. Dye-stained microparticles are easily prepared for in vivo near-infrared optical imaging using commercial imaging stations.

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Section: Resultsmentioning

confidence: 99%

Storable, thermally activated, near-infrared chemiluminescent dyes and dye-stained microparticles for optical imaging

et al. 2010

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“…The PL tail is the sum of two contributions from C 60 emission ͑mainly from deep traps 29,30 ͒ and Zn-Pc phosphorescence. [31][32][33][34][35][36][37] The peak at 0.97 eV, observed only in the sample exposed to air, is assigned to the emission from singlet oxygen O 2 ͑Ref. 29͒ that is populated, via energy transfer, from the photoinduced C 60 triplet state.…”

Section: B Photoluminescencementioning

confidence: 99%

Weak intrinsic charge transfer complexes: A new route for developing wide spectrum organic photovoltaic cells

Ruani¹,

Fontanini²,

Murgia³

et al. 2002

The Journal of Chemical Physics

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Solar emission extends in the near IR and one of the main issues in designing organic solar cells resides in extending the response into the near IR. Here we show that this may be achieved by making intimate interpenetrated networks of C 60 and Zn-phthalocyanine ͑Zn-Pc͒ in the solid. Various spectroscopic investigations of co-sublimated thin films of C 60 and Zn-phthalocyanine give indeed ample evidence of the existence of a weak charge transfer ͑CT͒ state at 1.4 eV, which quenches the photoluminescence of both molecules. The films produced by co-sublimation undergo to a spinodal decomposition producing domains prevalently constituted by Zn-Pc in contact with domain prevalently of C 60 . The domains size depends on the deposition conditions ͑rate, stoichiometry, and substrate temperature͒ forming a percolating 3D network. The separation in different domains is confirmed by the observation of two overlapping peaks, in the resonant Raman spectrum, that correspond to the A g (2) pinch mode ͑CvC double bond stretching͒ for pristine C 60 and for a partially (ϳ0.25e Ϫ ) doped one. This indicates that only those donor molecules at the grain boundary, which are in contact with C 60 , give rise to a renormalized new CT ground state. Photocurrent measurements of interpenetrated networks of C 60 and Zn-Pc show a linear dependence with respect to the incident light as a consequence of direct absorption within the CT state. The CT state favors the charge separation between the two components, when it is inserted as interface in the organic photovoltaic p -n junction thus increasing the efficiency of the device.

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“…Furthermore, cell survival depends on the dose concentration and on the nature of the substituent at the periphery of Pc ring ( Hofman et al, 2007 ). Complexes IXb and IXd contain Al metal, but the difference in their in vitro activity can be explained based on electron-donating toluene and bulky groups present in IXb are able to prevent the aggregation and in turn enhance the absorption of radiation and ROS generation ( Murphy et al, 1999 ; Huang et al, 2018 ). However, IXd has an electron withdrawing benzimidazole substituent which may not prevent the aggregation as like the electron-donating toluene group and hence lesser in vitro activity.…”

Section: Resultsmentioning

confidence: 99%

Symmetrically Substituted Zn and Al Phthalocyanines and Polymers for Photodynamic Therapy Application

Nemakal

Managa

et al. 2021

Front. Chem.

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N4 macrocyclic complexes of Al and Zn phthalocyanines with symmetrical imine and imidazole moiety at the periphery were synthesized. The synthesized ligands, complexes, and polymers were purified and characterized to study the structure of the molecule. These synthesized complexes were used for photodynamic therapy application as the diamagnetic Zn and Al have the ability to produce and stabilize singlet oxygen species. The synthesized N4 molecules of aluminum iminomethoxy phenyl phthalocyanine and aluminum ethyl phenyl benzimidazolephthalocyanine showed better activity against MCF-7 cells. These results suggest that this assay may be used as an early biomarker of clinical response.

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Singlet-Oxygen-Sensitized Delayed Fluorescence: Direct Detection of Triplet Phthalocyanine as an Intermediate

Cited by 30 publications

References 27 publications

Storable, thermally activated, near-infrared chemiluminescent dyes and dye-stained microparticles for optical imaging

Storable, thermally activated, near-infrared chemiluminescent dyes and dye-stained microparticles for optical imaging

Weak intrinsic charge transfer complexes: A new route for developing wide spectrum organic photovoltaic cells

Symmetrically Substituted Zn and Al Phthalocyanines and Polymers for Photodynamic Therapy Application

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