Dimethyl amino phenyl substituted silver phthalocyanine as a UV- and visible-light absorbing photoinitiator: <i>in situ</i> preparation of silver/polymer nanocomposites

Author(s): Louise Breloy ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Yusuf Alcay ⁶ ^, ⁷ ^, ⁸ ^, ⁹ , Ismail Yilmaz ⁶ ^, ⁷ ^, ⁸ ^, ⁹ , Martin Breza ¹⁰ ^, ¹¹ ^, ¹² ^, ¹³ ^, ¹⁴ , Julie Bourgon ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵ , Vlasta Brezová ¹⁰ ^, ¹¹ ^, ¹² ^, ¹³ ^, ¹⁴ , Yusuf Yagci ⁶ ^, ⁷ ^, ⁸ ^, ⁹ , Davy-Louis Versace ¹ ^, ² ^, ³ ^, ⁴ ^, ⁵

Publication date (Electronic): 2021

Journal: Polymer Chemistry

Publisher: Royal Society of Chemistry (RSC)

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Abstract

Synthesis of a novel phthalocyanine for dual free-radical and cationic photopolymerizations and the in situ preparation of nanocomposites without using metal salts.

Abstract

A novel visible-light absorbing silver dimethyl amino phenyl substituted phthalocyanine photoinitiator ( dmaph-Ag(II)Pc) for free-radical (FRP) and cationic (CP) polymerizations in laminate and under air is reported. The photoinduced electron transfer reactions of excited dmaph-Ag(II)Pc in the presence and absence of an iodonium salt (Iod) resulted in the formation of a Brønsted acid and radical species capable of initiating CP and FRP, respectively. The photophysical and photochemical properties of the photoinitiator are evaluated in detail by computational and spectroscopic investigations, and the kinetics of the polymerizations are studied. It was demonstrated that the described photoinitiating system is highly efficient in the simultaneous cationic or free-radical polymerization and silver ion reduction. The nanocomposites formed this way contain spherical shaped silver nanoparticles homogenously dispersed in the polymer matrix with a narrow size distribution between 5 and 20 nm.

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A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu.

Stefan Grimme, Jens Antony, Stephan Ehrlich … (2010)

The method of dispersion correction as an add-on to standard Kohn-Sham density functional theory (DFT-D) has been refined regarding higher accuracy, broader range of applicability, and less empiricism. The main new ingredients are atom-pairwise specific dispersion coefficients and cutoff radii that are both computed from first principles. The coefficients for new eighth-order dispersion terms are computed using established recursion relations. System (geometry) dependent information is used for the first time in a DFT-D type approach by employing the new concept of fractional coordination numbers (CN). They are used to interpolate between dispersion coefficients of atoms in different chemical environments. The method only requires adjustment of two global parameters for each density functional, is asymptotically exact for a gas of weakly interacting neutral atoms, and easily allows the computation of atomic forces. Three-body nonadditivity terms are considered. The method has been assessed on standard benchmark sets for inter- and intramolecular noncovalent interactions with a particular emphasis on a consistent description of light and heavy element systems. The mean absolute deviations for the S22 benchmark set of noncovalent interactions for 11 standard density functionals decrease by 15%-40% compared to the previous (already accurate) DFT-D version. Spectacular improvements are found for a tripeptide-folding model and all tested metallic systems. The rectification of the long-range behavior and the use of more accurate C(6) coefficients also lead to a much better description of large (infinite) systems as shown for graphene sheets and the adsorption of benzene on an Ag(111) surface. For graphene it is found that the inclusion of three-body terms substantially (by about 10%) weakens the interlayer binding. We propose the revised DFT-D method as a general tool for the computation of the dispersion energy in molecules and solids of any kind with DFT and related (low-cost) electronic structure methods for large systems.

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Density-functional thermochemistry. III. The role of exact exchange

Axel D. Becke (1993)

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Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions.

Aleksandr V Marenich, Christopher J. Cramer, Donald G Truhlar (2009)

We present a new continuum solvation model based on the quantum mechanical charge density of a solute molecule interacting with a continuum description of the solvent. The model is called SMD, where the "D" stands for "density" to denote that the full solute electron density is used without defining partial atomic charges. "Continuum" denotes that the solvent is not represented explicitly but rather as a dielectric medium with surface tension at the solute-solvent boundary. SMD is a universal solvation model, where "universal" denotes its applicability to any charged or uncharged solute in any solvent or liquid medium for which a few key descriptors are known (in particular, dielectric constant, refractive index, bulk surface tension, and acidity and basicity parameters). The model separates the observable solvation free energy into two main components. The first component is the bulk electrostatic contribution arising from a self-consistent reaction field treatment that involves the solution of the nonhomogeneous Poisson equation for electrostatics in terms of the integral-equation-formalism polarizable continuum model (IEF-PCM). The cavities for the bulk electrostatic calculation are defined by superpositions of nuclear-centered spheres. The second component is called the cavity-dispersion-solvent-structure term and is the contribution arising from short-range interactions between the solute and solvent molecules in the first solvation shell. This contribution is a sum of terms that are proportional (with geometry-dependent proportionality constants called atomic surface tensions) to the solvent-accessible surface areas of the individual atoms of the solute. The SMD model has been parametrized with a training set of 2821 solvation data including 112 aqueous ionic solvation free energies, 220 solvation free energies for 166 ions in acetonitrile, methanol, and dimethyl sulfoxide, 2346 solvation free energies for 318 neutral solutes in 91 solvents (90 nonaqueous organic solvents and water), and 143 transfer free energies for 93 neutral solutes between water and 15 organic solvents. The elements present in the solutes are H, C, N, O, F, Si, P, S, Cl, and Br. The SMD model employs a single set of parameters (intrinsic atomic Coulomb radii and atomic surface tension coefficients) optimized over six electronic structure methods: M05-2X/MIDI!6D, M05-2X/6-31G, M05-2X/6-31+G, M05-2X/cc-pVTZ, B3LYP/6-31G, and HF/6-31G. Although the SMD model has been parametrized using the IEF-PCM protocol for bulk electrostatics, it may also be employed with other algorithms for solving the nonhomogeneous Poisson equation for continuum solvation calculations in which the solute is represented by its electron density in real space. This includes, for example, the conductor-like screening algorithm. With the 6-31G basis set, the SMD model achieves mean unsigned errors of 0.6-1.0 kcal/mol in the solvation free energies of tested neutrals and mean unsigned errors of 4 kcal/mol on average for ions with either Gaussian03 or GAMESS.

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Author and article information

Contributors

Martin Breza: (View ORCID Profile)

Yusuf Yagci: (View ORCID Profile)

Davy-Louis Versace: (View ORCID Profile)

Journal

Journal ID (publisher-id): PCOHC2

Title: Polymer Chemistry

Abbreviated Title: Polym. Chem.

Publisher: Royal Society of Chemistry (RSC)

ISSN (Print): 1759-9954

ISSN (Electronic): 1759-9962

Publication date Created: March 9 2021

Publication date (Electronic): 2021

Volume: 12

Issue: 9

Pages: 1273-1285

Affiliations

[1 ]Institut de Chimie et de Matériaux Paris-Est (ICMPE)

[2 ]Equipe Systèmes Polymères Complexes

[3 ]CNRS-UPEC UMR 7182

[4 ]Thiais

[5 ]France

[6 ]Istanbul Technical University

[7 ]Department of Chemistry

[8 ]Istanbul

[9 ]Turkey

[10 ]Slovak University of Technology in Bratislava

[11 ]Faculty of Chemical and Food Technology

[12 ]Institute of Physical Chemistry and Chemical Physics

[13 ]Department of Physical Chemistry

[14 ]SK-812 37 Bratislava

Article

DOI: 10.1039/D0PY01712D

SO-VID: 7689b79e-a69c-4331-8908-9595ba0fe4e3

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Dimethyl amino phenyl substituted silver phthalocyanine as a UV- and visible-light absorbing photoinitiator: in situ preparation of silver/polymer nanocomposites

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Photoluminescent Nanomaterials

Most cited references 70

A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu.

Density-functional thermochemistry. III. The role of exact exchange

Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions.

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