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Title: Absorption and Fluorescence Features of an Amphiphilic meso-Pyrimidinylcorrole: Experimental Study and Quantum Chemical Calculations

Abstract

Here corroles are emerging as an important class of macrocycles with numerous applications because of their peculiar photophysical and metal chelating properties. meso-Pyrimidinylcorroles are easily deprotonated in certain solvents, which changes their absorption and emission spectra as well as their accessible supramolecular structures. To enable control over the formation of supramolecular structures, the dominant corrole species, i.e., the deprotonated form or one of the two NH-tautomers, needs to be identified. Therefore, we focus in the present article on the determination of the UV–vis spectroscopic properties of the free-base NH-tautomers and the deprotonated form of a new amphiphilic meso-pyrimidinylcorrole that can assemble to supramolecular structures at heterointerfaces as utilized in the Langmuir–Blodgett and liquid–liquid interface precipitation techniques. After quantification of the polarities of the free-base NH-tautomers and the deprotonated form by means of quantum chemically derived electrostatic potential distributions at the corroles’ van der Waals surfaces, the preferential stabilization of (some of) the considered species in solvents of different polarity is identified by means of absorption spectroscopy. For the solutions with complex mixtures of species, we applied fluorescence excitation spectroscopy to estimate the relative weights of the individual corrole species. This technique might also be applied to identify dominating species inmore » molecularly thin films directly on the subphase’ surface of Langmuir–Blodgett troughs. Supported by quantum chemical calculations we were able to differentiate between the spectral signatures of the individual NH-tautomers by means of fluorescence excitation spectroscopy.« less

Authors:
ORCiD logo [1]; ORCiD logo [1];  [2]; ORCiD logo [3]; ORCiD logo [4]; ORCiD logo [5]; ORCiD logo [2];  [6]; ORCiD logo [7]; ORCiD logo [8]
+ Show Author Affiliations
  1. Friedrich Schiller Univ. Jena, Jena (Germany); Leibniz Institute of Photonic Technology (IPHT), Jena (Germany)
  2. National Institute for Material Science, Ibaraki (Japan)
  3. SLAC National Accelerator Lab., Menlo Park, CA (United States); Stanford Univ., Stanford, CA (United States)
  4. Friedrich Schiller Univ. Jena, Jena (Germany); Leibniz Institute of Photonic Technology (IPHT), Jena (Germany); Center for Energy and Environmental Chemistry Jena (CEEC Jena), Jena (Germany)
  5. National Institute for Materials Science, Ibaraki (Japan)
  6. Belarusian State Technological Univ., Minsk (Belarus)
  7. UHasselt - Hasselt Univ., Diepenbeek (Belgium)
  8. Friedrich Schiller Univ. Jena, Jena (Germany); Leibniz Institute of Photonic Technology (IPHT), Jena (Germany); Center for Energy and Environmental Chemistry Jena (CEEC Jena), Jena (Germany); Sciclus GmbH Co., Jena (Germany)
Publication Date:
Research Org.:
SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1463313
Grant/Contract Number:  
AC02-76SF00515; 03EK3507; JP16H06518
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory
Additional Journal Information:
Journal Volume: 121; Journal Issue: 45; Journal ID: ISSN 1089-5639
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Preiß, Julia, Herrmann-Westendorf, Felix, Ngo, Thien H., Martínez, Todd, Dietzek, Benjamin, Hill, Jonathan P., Ariga, Katsuhiko, Kruk, Mikalai M., Maes, Wouter, and Presselt, Martin. Absorption and Fluorescence Features of an Amphiphilic meso-Pyrimidinylcorrole: Experimental Study and Quantum Chemical Calculations. United States: N. p., 2017. Web. doi:10.1021/acs.jpca.7b08910.
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Preiß, Julia, Herrmann-Westendorf, Felix, Ngo, Thien H., Martínez, Todd, Dietzek, Benjamin, Hill, Jonathan P., Ariga, Katsuhiko, Kruk, Mikalai M., Maes, Wouter, & Presselt, Martin. Absorption and Fluorescence Features of an Amphiphilic meso-Pyrimidinylcorrole: Experimental Study and Quantum Chemical Calculations. United States. https://doi.org/10.1021/acs.jpca.7b08910
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Preiß, Julia, Herrmann-Westendorf, Felix, Ngo, Thien H., Martínez, Todd, Dietzek, Benjamin, Hill, Jonathan P., Ariga, Katsuhiko, Kruk, Mikalai M., Maes, Wouter, and Presselt, Martin. Wed . "Absorption and Fluorescence Features of an Amphiphilic meso-Pyrimidinylcorrole: Experimental Study and Quantum Chemical Calculations". United States. https://doi.org/10.1021/acs.jpca.7b08910. https://www.osti.gov/servlets/purl/1463313.
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@article{osti_1463313,
title = {Absorption and Fluorescence Features of an Amphiphilic meso-Pyrimidinylcorrole: Experimental Study and Quantum Chemical Calculations},
author = {Preiß, Julia and Herrmann-Westendorf, Felix and Ngo, Thien H. and Martínez, Todd and Dietzek, Benjamin and Hill, Jonathan P. and Ariga, Katsuhiko and Kruk, Mikalai M. and Maes, Wouter and Presselt, Martin},
abstractNote = {Here corroles are emerging as an important class of macrocycles with numerous applications because of their peculiar photophysical and metal chelating properties. meso-Pyrimidinylcorroles are easily deprotonated in certain solvents, which changes their absorption and emission spectra as well as their accessible supramolecular structures. To enable control over the formation of supramolecular structures, the dominant corrole species, i.e., the deprotonated form or one of the two NH-tautomers, needs to be identified. Therefore, we focus in the present article on the determination of the UV–vis spectroscopic properties of the free-base NH-tautomers and the deprotonated form of a new amphiphilic meso-pyrimidinylcorrole that can assemble to supramolecular structures at heterointerfaces as utilized in the Langmuir–Blodgett and liquid–liquid interface precipitation techniques. After quantification of the polarities of the free-base NH-tautomers and the deprotonated form by means of quantum chemically derived electrostatic potential distributions at the corroles’ van der Waals surfaces, the preferential stabilization of (some of) the considered species in solvents of different polarity is identified by means of absorption spectroscopy. For the solutions with complex mixtures of species, we applied fluorescence excitation spectroscopy to estimate the relative weights of the individual corrole species. This technique might also be applied to identify dominating species in molecularly thin films directly on the subphase’ surface of Langmuir–Blodgett troughs. Supported by quantum chemical calculations we were able to differentiate between the spectral signatures of the individual NH-tautomers by means of fluorescence excitation spectroscopy.},
doi = {10.1021/acs.jpca.7b08910},
journal = {Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory},
number = 45,
volume = 121,
place = {United States},
year = {Wed Oct 25 00:00:00 EDT 2017},
month = {Wed Oct 25 00:00:00 EDT 2017}
}
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https://doi.org/10.1021/acs.jpca.7b08910
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Works referenced in this record:

Phosphorescence of free base corroles
journal, January 2016

  • Knyukshto, Valeriy N.; Ngo, Thien Huynh; Dehaen, Wim
  • RSC Advances, Vol. 6, Issue 50
  • DOI: 10.1039/C6RA06196F

The impact of solvents on the singlet and triplet states of selected fluorine corroles – absorption, fluorescence, and optoacoustic studies
journal, January 2016

  • Bursa, Bartosz; Wróbel, Danuta; Barszcz, Bolesław
  • Physical Chemistry Chemical Physics, Vol. 18, Issue 10
  • DOI: 10.1039/C5CP06335C

β-Nitro-5,10,15-tritolylcorroles
journal, June 2012

  • Stefanelli, Manuela; Pomarico, Giuseppe; Tortora, Luca
  • Inorganic Chemistry, Vol. 51, Issue 12
  • DOI: 10.1021/ic3007926

Coordination chemistry of corroles with focus on main group elements
journal, April 2011

Photoactive corrole-based arrays
journal, January 2009

  • Flamigni, Lucia; Gryko, Daniel T.
  • Chemical Society Reviews, Vol. 38, Issue 6
  • DOI: 10.1039/b805230c

Pyrolyzed Cobalt Corrole as a Potential Non-Precious Catalyst for Fuel Cells
journal, May 2012

  • Huang, Hsin-Chih; Shown, Indrajit; Chang, Sun-Tang
  • Advanced Functional Materials, Vol. 22, Issue 16
  • DOI: 10.1002/adfm.201200264

Metallocorroles as Nonprecious-Metal Catalysts for Oxygen Reduction
journal, October 2015

  • Levy, Naomi; Mahammed, Atif; Kosa, Monica
  • Angewandte Chemie International Edition, Vol. 54, Issue 47
  • DOI: 10.1002/anie.201505236

A Bifunctional Electrocatalyst for Oxygen Evolution and Oxygen Reduction Reactions in Water
journal, January 2016

  • Schöfberger, Wolfgang; Faschinger, Felix; Chattopadhyay, Samir
  • Angewandte Chemie International Edition, Vol. 55, Issue 7
  • DOI: 10.1002/anie.201508404

Metallocorroles as Non-Precious Metal Electrocatalysts for Highly Efficient Oxygen Reduction in Alkaline Media
journal, August 2016

Fighting Cancer with Corroles
journal, October 2016

Photodynamic effects induced by meso-tris(pentafluorophenyl)corrole and its cyclodextrin conjugates on cytoskeletal components of HeLa cells
journal, March 2015

  • Barata, Joana F. B.; Zamarrón, Alicia; Neves, M. Graça P. M. S.
  • European Journal of Medicinal Chemistry, Vol. 92
  • DOI: 10.1016/j.ejmech.2014.12.025

Tumor detection and elimination by a targeted gallium corrole
journal, April 2009

  • Agadjanian, H.; Ma, J.; Rentsendorj, A.
  • Proceedings of the National Academy of Sciences, Vol. 106, Issue 15
  • DOI: 10.1073/pnas.0901531106

Selective Chemisorption of Carbon Monoxide by Organic–Inorganic Hybrid Materials Incorporating Cobalt(III) Corroles as Sensing Components
journal, February 2007

  • Barbe, Jean-Michel; Canard, Gabriel; Brandès, Stéphane
  • Chemistry - A European Journal, Vol. 13, Issue 7
  • DOI: 10.1002/chem.200601143

Supramolecular sensing mechanism of corrole thin films
journal, October 2013

Corrole and Corrole Functionalized Silica Nanoparticles as New Metal Ion Chemosensors: A Case of Silver Satellite Nanoparticles Formation
journal, July 2013

  • Santos, Carla I. M.; Oliveira, Elisabete; Fernández-Lodeiro, Javier
  • Inorganic Chemistry, Vol. 52, Issue 15
  • DOI: 10.1021/ic4006295

Photometric Detection of Nitric Oxide Using a Dissolved Iron(III) Corrole as a Sensitizer
journal, February 2016

Porphyrinoids for Chemical Sensor Applications
journal, October 2016

Gold(III) Corroles for High Performance Organic Solar Cells
journal, April 2014

  • Lai, Shiu-Lun; Wang, Lin; Yang, Chen
  • Advanced Functional Materials, Vol. 24, Issue 29
  • DOI: 10.1002/adfm.201400082

Gold Tris(carboxyphenyl)corroles as Multifunctional Materials: Room Temperature Near-IR Phosphorescence and Applications to Photodynamic Therapy and Dye-Sensitized Solar Cells
journal, July 2016

  • Alemayehu, Abraham B.; Day, Nicholas U.; Mani, Tomoyasu
  • ACS Applied Materials & Interfaces, Vol. 8, Issue 29
  • DOI: 10.1021/acsami.6b04269

Photoelectrochemical Cells Utilizing Tunable Corroles
journal, July 2015

  • Brennan, Bradley J.; Lam, Yick Chong; Kim, Paul M.
  • ACS Applied Materials & Interfaces, Vol. 7, Issue 29
  • DOI: 10.1021/acsami.5b05050

Metamorphosis of Tetrapyrrole Macrocycles
journal, November 2006

  • Senge, Mathias O.; Sergeeva, Natalia N.
  • Angewandte Chemie International Edition, Vol. 45, Issue 45
  • DOI: 10.1002/anie.200603249

N - H tautomerization in triaryl corroles
journal, January 2005

  • Ding, Tang; Harvey, John D.; Ziegler, Christopher J.
  • Journal of Porphyrins and Phthalocyanines, Vol. 09, Issue 01
  • DOI: 10.1142/S1088424605000058

Solvent-Dependent Deprotonation of meso -Pyrimidinylcorroles: Absorption and Fluorescence Studies
journal, September 2012

  • Kruk, Mikalai; Ngo, Thien H.; Savva, Vadim
  • The Journal of Physical Chemistry A, Vol. 116, Issue 44
  • DOI: 10.1021/jp305327c

Unraveling the Fluorescence Features of Individual Corrole NH Tautomers
journal, September 2012

  • Kruk, Mikalai; Ngo, Thien H.; Verstappen, Pieter
  • The Journal of Physical Chemistry A, Vol. 116, Issue 44
  • DOI: 10.1021/jp305326x

Molecular Structures and Absorption Spectra Assignment of Corrole NH Tautomers
journal, January 2014

  • Beenken, Wichard; Presselt, Martin; Ngo, Thien H.
  • The Journal of Physical Chemistry A, Vol. 118, Issue 5
  • DOI: 10.1021/jp411033h

Origin of the Individual Basicity of Corrole NH-Tautomers: A Quantum Chemical Study on Molecular Structure and Dynamics, Kinetics, and Thermodynamics
journal, June 2015

  • Beenken, Wichard; Maes, Wouter; Kruk, Mikalai
  • The Journal of Physical Chemistry A, Vol. 119, Issue 26
  • DOI: 10.1021/acs.jpca.5b02869

Corrole NH Tautomers: Spectral Features and Individual Protonation
journal, September 2012

  • Ivanova, Yulia B.; Savva, Vadim A.; Mamardashvili, Nugzar Z.
  • The Journal of Physical Chemistry A, Vol. 116, Issue 44
  • DOI: 10.1021/jp305325e

Monolayer Studies of Single-Chain Polyprenyl Phosphates
journal, May 2005

  • Ariga, Katsuhiko; Yuki, Harufumi; Kikuchi, Jun-ichi
  • Langmuir, Vol. 21, Issue 10
  • DOI: 10.1021/la0467887

Structural Characterizations of C 60 -Derivative Langmuir−Blodgett Films and Their Photovoltaic Behaviors
journal, June 1999

Aggregation properties of tetrachloroperylene-tetracarboxylic acid in binary Langmuir and Langmuir–Blodgett films
journal, April 2014

The Langmuir-Blodgett Technique as a Tool for Homeotropic Alignment of Fluorinated Liquid Crystals Mixed with Arachidic Acid
journal, August 2011

  • Modlińska, Anna; Bauman, Danuta
  • International Journal of Molecular Sciences, Vol. 12, Issue 8
  • DOI: 10.3390/ijms12084923

Controlling Electronic Transitions in Fullerene van der Waals Aggregates via Supramolecular Assembly
journal, August 2016

  • Das, Saunak; Herrmann-Westendorf, Felix; Schacher, Felix H.
  • ACS Applied Materials & Interfaces, Vol. 8, Issue 33
  • DOI: 10.1021/acsami.6b06800

Size-Tunable Hexagonal Fullerene (C 60 ) Nanosheets at the Liquid−Liquid Interface
journal, November 2007

  • Sathish, Marappan; Miyazawa, Kun'ichi
  • Journal of the American Chemical Society, Vol. 129, Issue 45
  • DOI: 10.1021/ja076251q

meso -Pyrimidinyl-Substituted A 2 B-Corroles
journal, July 2007

  • Maes, Wouter; Ngo, Thien H.; Vanderhaeghen, Jeroen
  • Organic Letters, Vol. 9, Issue 16
  • DOI: 10.1021/ol071226a

Reductive demetallation of Cu-corroles—a new protective strategy towards functional free-base corroles
journal, January 2009

  • Ngo, Thien Huynh; Van Rossom, Wim; Dehaen, Wim
  • Org. Biomol. Chem., Vol. 7, Issue 3
  • DOI: 10.1039/B819185A

meso -Pyrimidinyl-Substituted A 2 B- and A 3 -Corroles
journal, February 2010

  • Ngo, Thien H.; Nastasi, Francesco; Puntoriero, Fausto
  • The Journal of Organic Chemistry, Vol. 75, Issue 6
  • DOI: 10.1021/jo902709c

Synthetic, Structural, and Photophysical Exploration of meso -Pyrimidinyl-Substituted AB 2 -Corroles
journal, April 2010

  • Ngo, Thien H.; Puntoriero, Fausto; Nastasi, Francesco
  • Chemistry - A European Journal, Vol. 16, Issue 19
  • DOI: 10.1002/chem.201000008

Corrole-Porphyrin Conjugates with Interchangeable Metal Centers
journal, August 2012

  • Ngo, Thien H.; Nastasi, Francesco; Puntoriero, Fausto
  • European Journal of Organic Chemistry, Vol. 2012, Issue 28
  • DOI: 10.1002/ejoc.201200836

Ab initio effective core potentials for molecular calculations. Potentials for main group elements Na to Bi
journal, January 1985

  • Wadt, Willard R.; Hay, P. Jeffrey
  • The Journal of Chemical Physics, Vol. 82, Issue 1
  • DOI: 10.1063/1.448800

Organic Electronic Materials: Recent Advances in the DFT Description of the Ground and Excited States Using Tuned Range-Separated Hybrid Functionals
journal, April 2014

  • Körzdörfer, Thomas; Brédas, Jean-Luc
  • Accounts of Chemical Research, Vol. 47, Issue 11
  • DOI: 10.1021/ar500021t

Fundamental and excitation gaps in molecules of relevance for organic photovoltaics from an optimally tuned range-separated hybrid functional
journal, August 2011

Assessment of the performance of tuned range-separated hybrid density functionals in predicting accurate quasiparticle spectra
journal, November 2012

Excited-State Electronic Structure with Configuration Interaction Singles and Tamm–Dancoff Time-Dependent Density Functional Theory on Graphical Processing Units
journal, May 2011

  • Isborn, Christine M.; Luehr, Nathan; Ufimtsev, Ivan S.
  • Journal of Chemical Theory and Computation, Vol. 7, Issue 6
  • DOI: 10.1021/ct200030k

Electronic spectra from molecular dynamics: a simple approach
journal, February 1984

  • Bergsma, John P.; Berens, Peter H.; Wilson, Kent R.
  • The Journal of Physical Chemistry, Vol. 88, Issue 3
  • DOI: 10.1021/j150647a055

Spectrum simulation and decomposition with nuclear ensemble: formal derivation and application to benzene, furan and 2-phenylfuran
journal, June 2012

Electronic Absorption Spectra from MM and ab Initio QM/MM Molecular Dynamics: Environmental Effects on the Absorption Spectrum of Photoactive Yellow Protein
journal, September 2012

  • Isborn, Christine M.; Götz, Andreas W.; Clark, Matthew A.
  • Journal of Chemical Theory and Computation, Vol. 8, Issue 12
  • DOI: 10.1021/ct3006826

Half-numerical evaluation of pseudopotential integrals
journal, January 2006

  • Flores-Moreno, Roberto; Alvarez-Mendez, Rodrigo J.; Vela, Alberto
  • Journal of Computational Chemistry, Vol. 27, Issue 9
  • DOI: 10.1002/jcc.20410

A Concept to Tailor Electron Delocalization: Applying QTAIM Analysis to Phenyl−Terpyridine Compounds
journal, December 2010

  • Presselt, Martin; Dietzek, Benjamin; Schmitt, Michael
  • The Journal of Physical Chemistry A, Vol. 114, Issue 50
  • DOI: 10.1021/jp107007a

Derivation of Correlation Functions to Predict Bond Properties of Phenyl−CH Bonds Based on Vibrational and 1 H NMR Spectroscopic Quantities
journal, September 2010

  • Presselt, Martin; Schnedermann, Christoph; Müller, Michael
  • The Journal of Physical Chemistry A, Vol. 114, Issue 37
  • DOI: 10.1021/jp105348d

Steric and electronic contributions to the core reactivity of monoprotonated 5-phenylporphyrin: A DFT study
journal, May 2014

Quantum chemical insights into the dependence of porphyrin basicity on the meso-aryl substituents: thermodynamics, buckling, reaction sites and molecular flexibility
journal, January 2015

  • Presselt, Martin; Dehaen, Wim; Maes, Wouter
  • Physical Chemistry Chemical Physics, Vol. 17, Issue 21
  • DOI: 10.1039/C5CP01808K

COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient
journal, January 1993

Accurate prediction of basicity in aqueous solution with COSMO-RS
journal, January 2005

  • Eckert, Frank; Klamt, Andreas
  • Journal of Computational Chemistry, Vol. 27, Issue 1
  • DOI: 10.1002/jcc.20309

A survey of Hammett substituent constants and resonance and field parameters
journal, March 1991

  • Hansch, Corwin.; Leo, A.; Taft, R. W.
  • Chemical Reviews, Vol. 91, Issue 2
  • DOI: 10.1021/cr00002a004

The Effect of Structure upon the Reactions of Organic Compounds. Benzene Derivatives
journal, January 1937

  • Hammett, Louis P.
  • Journal of the American Chemical Society, Vol. 59, Issue 1
  • DOI: 10.1021/ja01280a022

Solvent effects on chemical reactivity. Evaluation of anion- and cation-solvation components
journal, February 1983

  • Swain, C. Gardner; Swain, Marguerite S.; Powell, Arnet L.
  • Journal of the American Chemical Society, Vol. 105, Issue 3
  • DOI: 10.1021/ja00341a033

A Reëxamination of the Hammett Equation.
journal, October 1953

Sub-bandgap absorption in organic solar cells: experiment and theory
journal, January 2013

  • Beenken, Wichard J. D.; Herrmann, Felix; Presselt, Martin
  • Physical Chemistry Chemical Physics, Vol. 15, Issue 39
  • DOI: 10.1039/c3cp42236d

Stable and Easily Accessible Functional Dyes: Dihydrotetraazaanthracenes as Versatile Precursors for Higher Acenes
journal, April 2015

  • Gampe, Dominique Mario; Kaufmann, Martin; Jakobi, Dörthe
  • Chemistry - A European Journal, Vol. 21, Issue 20
  • DOI: 10.1002/chem.201500230

Quantum Chemistry for Solvated Molecules on Graphical Processing Units Using Polarizable Continuum Models
journal, June 2015

  • Liu, Fang; Luehr, Nathan; Kulik, Heather J.
  • Journal of Chemical Theory and Computation, Vol. 11, Issue 7
  • DOI: 10.1021/acs.jctc.5b00370
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