Synthesis, spectroscopy, and photophysics of porphyrins attached to gold nanoparticles<i>via</i>one or two linkers

Buczyńska, Joanna; Pszona, Maria; Kowalska, Patrycja; Waluk, Jacek

doi:10.1142/s1088424614500424

Cited by 4 publications

(6 citation statements)

References 24 publications

(22 reference statements)

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“…For an extreme case of d SiO2 = 0, i.e. the chromophore-NP distance of 0.7 nm, the calculations predict the lifetime decrease of about two orders of magnitude, in perfect agreement with the experimental results [37]. The dependence on the core radius seems to be weaker; however, this is not the case for d SiO2 less than about 5 nm.…”

Section: Emission Enhancementsupporting

confidence: 79%

“…The intrinsic photophysical parameters of the chromophore were taken from our experimental work on meso-tetraphenylporphyrin singly substituted with a thiocarbamate group [37]: Absorption coefficients, emission spectrum, fluorescence lifetime, τ 0 = 7.96 ns, fluorescence quantum yield, ϕ 0 = 0.094. These values imply k rad 0 = 1.18 × 10 7 s −1 and k nr = 1.14 × 10 8 s −1 .…”

Section: Resultsmentioning

confidence: 99%

“…The systems studied so far include gold nano-particles coated with a horizontal porphyrin monolayer [26], gold clusters stabilized by porphyrin-alkanethiolate [27][28][29], free-base porphyrins with two thioacetate-terminated linkers attached to AuNPs stabilized by tetraoctylammonium bromide [30], AuNP-porphyrin self-assembled multistructures for photoelectric conversion [31], 2D assemblies of tetrapyridylporphyrinderivatized gold nanoparticles (AuNPs) [32], zinc metalloporphyrin-functionalized nanoparticle anion sensors [33], thiol-derivatized cobalt porphyrins on gold surfaces [34], gold(0) porphyrins on gold nanoparticles [35], and water-soluble gold nanoparticles protected by meso-tetraphenylporphyrin-thiol derivative [36]. In our recent work, four novel meso-tetraphenylporphyrin derivatives bearing thiocarbamate or thioacetate linkers were synthesized and subsequently attached to gold nanoparticles [37]. A large decrease in fluorescence decay time and a change in the spectral profile of fluorescence were observed for these systems.…”

Section: Introductionmentioning

confidence: 99%

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Simulations of fluorescence enhancement and emission profile changes in porphyrin attached to gold-silica core–shell nanoparticles

Kelm

Waluk

2015

Methods Appl. Fluoresc.

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Changes in the spectral and photophysical parameters of a porphyrin derivative caused by placing the molecule in the vicinity of a spherical gold or core–shell gold-silica nanoparticle have been predicted using Mie theory. The simulations allow the optimization of the system with regard to maximum brightness enhancement. The results demonstrate that, in addition to fluorescence quantum yield and decay time, the spectral emission profile may also be modified by an appropriate choice of the nanoparticle parameters, such as gold core radius and shell thickness. Both emission intensity and shape are also dependent on the relative orientation of the molecular transition dipole moment with respect to the nanoparticle surface.

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Section: Emission Enhancementsupporting

confidence: 79%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Simulations of fluorescence enhancement and emission profile changes in porphyrin attached to gold-silica core–shell nanoparticles

Kelm

Waluk

2015

Methods Appl. Fluoresc.

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“…It will be fascinating to check whether the influence of plasmonic environment is limited to photophysical properties or if it also affects the proton transfer mechanisms. Our recent work on porphyrins attached to gold nanoparticles predict that not only the fluorescence yield and lifetime of such chromophores, but also the spectral shape may vary [141,142]. Since the transition moment direction changes as a result of proton transfer, it is realistic to expect different spectral, photophysical, but also chemical characteristics for the two tautomers, no longer equivalent in the plasmonic environments.…”

Section: Discussionmentioning

confidence: 99%

Non-typical fluorescence studies of excited and ground state proton and hydrogen transfer

Gil

Kijak

Piwoński

et al. 2017

Methods Appl. Fluoresc.

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Fluorescence studies of tautomerization have been carried out for various systems that exhibit single and double proton or hydrogen translocation in various environments, such as liquid and solid condensed phases, ultracold supersonic jets, and finally, polymer matrices with single emitters. We focus on less explored areas of application of fluorescence for tautomerization studies, using porphycene, a porphyrin isomer, as an example. Fluorescence anisotropy techniques allow investigations of self-exchange reactions, where the reactant and product are formally identical. Excitation with polarized light makes it possible to monitor tautomerization in single molecules and to detect their three-dimensional orientation. Analysis of fluorescence from single vibronic levels of jet-isolated porphycene not only demonstrates coherent tunneling of two internal protons, but also indicates that the process is vibrational mode-specific. Next, we present bifunctional proton donor-acceptor systems, molecules that are able, depending on the environment, to undergo excited state single intramolecular or double intermolecular proton transfer. For molecules that have donor and acceptor groups located in separate moieties linked by a single bond, excited state tautomerization can be coupled to mutual twisting of the two subunits.

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“…Studies on the synthesis, structure, spectroscopy and photodynamics of macrocycles such as porphyrin, phthalocyanine, and chlorin have increased in importance in the last decades. This interest is mainly due to their catalytic, spectrophotometric, magnetic, and electrochemical properties, which enable these compounds to be employed in many different applications …”

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confidence: 99%

Quantum‐chemistry descriptors for photosensitizers based on macrocycles

et al. 2017

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Studies on the synthesis, structure, spectroscopy and photodynamics of macrocycles such as porphyrin, phthalocyanine, and chlorin have increased in importance in the last decades. This interest is mainly due to their catalytic, spectrophotometric, magnetic, and electrochemical properties, which enable these compounds to be employed in many different applications. [1][2][3][4][5][6] In combination with experimental approaches, theoretical studies based on quantum mechanics are useful for the comprehension of electronic structure and environmental effects. [2,[7][8][9][10][11][12][13][14][15][16][17][18] There are two main methodologies that aim to increase the efficiency for energy transfer appliances: complexation with different metallic ions and the addition of (a) polar/(un)charged substituents. Both methodologies are able to avoid the aggregation and/or enhance the substrate interaction while maintaining or even improving photochemical properties.[2,7-9,19-33]One of the first ab initio studies for porphyrins [34] was performed through the MO-LCGO-SCF method, described by Roothaan. [35][36][37] Since then, the number of ab initio studies for these macrocycles has grown significantly, particularly concerning the calculations based on density functional theory (DFT), due to its good relation and cost/accuracy ratio. [2,8,9,[17][18][19][20][21][22][23]25,26,28,29,31,[38][39][40][41][42][43][44][45][46][47] DFT studies of most porphyrins and phthalocyanines have employed B3LYP functio nal; [2,8,9,25,28,[38][39][40]48] nevertheless, other functionals such as BLYP, [8,29,49] VWN-B-P, [26] and BHandHLYP [8] have also been used. T. E. Shubina and T. Clark [25] performed a methodological study for porphyrins complexed to Fe(III) and Co(II), which indicated that B3LYP and OLYP functionals are excellent choices for studying these macrocycles. Time-dependent Hartree-Fock, [26,38,[41][42][43] ZINDO/S, [38,42] configuration interaction, [41,42] and CASSCF/CASPT2Phthalocyanines, porphyrins, and chlorins have been widely studied as photosensitizers. Both experimental and computational strategies are employed in order to propose new and more active molecules derived from those macrocycles. In this context, there are two main strategies used: (i) the addition of different substituents and (ii) the complexation of the macrocycle with different metallic ions. In this work, we present selected descriptors based on quantum chemistry calculations for forty macrocycles, including some approved drugs. We have found that density functional theory is a suitable methodology to study the large sets of molecules when applying the B3LYP/LanL2DZ methodology for geometry optimization and TD-OLYP/6-31G(d) for absorption spectrum. The inclusion of solvent effects by means of continuum model is important in order to obtain the accurate electronic data. We have verified that by bonding charged or polar substituents to the macrocycle, it is possible to enhance water solvation as well as to improve spectroscopic properties because molecular orbital...

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Synthesis, spectroscopy, and photophysics of porphyrins attached to gold nanoparticlesviaone or two linkers

Cited by 4 publications

References 24 publications

Simulations of fluorescence enhancement and emission profile changes in porphyrin attached to gold-silica core–shell nanoparticles

Simulations of fluorescence enhancement and emission profile changes in porphyrin attached to gold-silica core–shell nanoparticles

Non-typical fluorescence studies of excited and ground state proton and hydrogen transfer

Quantum‐chemistry descriptors for photosensitizers based on macrocycles

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