Insights into the photoinduced anion translocation of donor-π-acceptor (ion) molecules

By strategic design and synthesis of a new series of phosphonium salts (compounds 1-7[OTf] ), where [OTf] − stands for the trifluoromethanesulfonate anion, we performed comprehensive spectroscopic and dynamic studies on the photoinduced anion migration in toluene. Our aim is to probe if the anion mi...

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Published inChemical science (Cambridge) Vol. 15; no. 47; pp. 245 - 255
Main Authors Qu, Hao-Ting, Partanen, Iida, Chang, Kai-Hsin, Lin, Yan-Ding, Koshevoy, Igor O, Belyaev, Andrey, Chou, Pi-Tai
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 04.12.2024
Royal Society of Chemistry
The Royal Society of Chemistry
Subjects
Anions
Charge transfer
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Electron distribution
Excitation spectra
Ion migration
Physical Sciences
Response functions
Science & Technology
Spectral sensitivity
Toluene
REACTION-RATES
NEGATIVE SOLVATOCHROMISM
SHUTTLING DYNAMICS
DONOR
SOLVATION DYNAMICS
ACCEPTOR BIPHENYLS
INTRAMOLECULAR CHARGE-TRANSFER
COUNTERION MIGRATION
ELECTRONIC-STRUCTURE
EXCITED-STATES
Online AccessGet full text
ISSN2041-6520
2041-6539
2041-6539
DOI10.1039/d4sc04738a

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Abstract By strategic design and synthesis of a new series of phosphonium salts (compounds 1-7[OTf] ), where [OTf] − stands for the trifluoromethanesulfonate anion, we performed comprehensive spectroscopic and dynamic studies on the photoinduced anion migration in toluene. Our aim is to probe if the anion migration is associated with an intrinsic barrier or is barrier-free. After the occurrence of excited-state intramolecular charge transfer (ESICT) in 1-7 , the charge redistribution of the cation triggers the translocation of the counter anion [OTf] − , resulting in emission spectral temporal evolution. As a result, we describe the photoinduced anion migration by introducing spectral response function C ( t ), a concept adopted from the solvent diffusional relaxation. The experimental results indicate that the anion migration lacks an intrinsic barrier, i.e. , the relaxation dynamics can be described by a biased Brownian motion along the charge transfer direction. The experimental findings are also qualitatively supported by theoretical calculations including restrained electrostatic potential (RESP) and hole-electron distribution analyses. Compared to solvent relaxation in polar solvents, anion migration in toluene occurs at a much slower rate ( C ( t ) analysis) and primarily involves translational motion of anion from the donor to the acceptor.
AbstractList By strategic design and synthesis of a new series of phosphonium salts (compounds 1-7[OTf]), where [OTf] stands for the trifluoromethanesulfonate anion, we performed comprehensive spectroscopic and dynamic studies on the photoinduced anion migration in toluene. Our aim is to probe if the anion migration is associated with an intrinsic barrier or is barrier-free. After the occurrence of excited-state intramolecular charge transfer (ESICT) in 1-7, the charge redistribution of the cation triggers the translocation of the counter anion [OTf] , resulting in emission spectral temporal evolution. As a result, we describe the photoinduced anion migration by introducing spectral response function ( ), a concept adopted from the solvent diffusional relaxation. The experimental results indicate that the anion migration lacks an intrinsic barrier, , the relaxation dynamics can be described by a biased Brownian motion along the charge transfer direction. The experimental findings are also qualitatively supported by theoretical calculations including restrained electrostatic potential (RESP) and hole-electron distribution analyses.
By strategic design and synthesis of a new series of phosphonium salts (compounds 1–7[OTf]), where [OTf]− stands for the trifluoromethanesulfonate anion, we performed comprehensive spectroscopic and dynamic studies on the photoinduced anion migration in toluene. Our aim is to probe if the anion migration is associated with an intrinsic barrier or is barrier-free. After the occurrence of excited-state intramolecular charge transfer (ESICT) in 1–7, the charge redistribution of the cation triggers the translocation of the counter anion [OTf]−, resulting in emission spectral temporal evolution. As a result, we describe the photoinduced anion migration by introducing spectral response function C(t), a concept adopted from the solvent diffusional relaxation. The experimental results indicate that the anion migration lacks an intrinsic barrier, i.e., the relaxation dynamics can be described by a biased Brownian motion along the charge transfer direction. The experimental findings are also qualitatively supported by theoretical calculations including restrained electrostatic potential (RESP) and hole–electron distribution analyses.
By strategic design and synthesis of a new series of phosphonium salts (compounds 1-7[OTf]), where [OTf]- stands for the trifluoromethanesulfonate anion, we performed comprehensive spectroscopic and dynamic studies on the photoinduced anion migration in toluene. Our aim is to probe if the anion migration is associated with an intrinsic barrier or is barrier-free. After the occurrence of excited-state intramolecular charge transfer (ESICT) in 1-7, the charge redistribution of the cation triggers the translocation of the counter anion [OTf]-, resulting in emission spectral temporal evolution. As a result, we describe the photoinduced anion migration by introducing spectral response function C(t), a concept adopted from the solvent diffusional relaxation. The experimental results indicate that the anion migration lacks an intrinsic barrier, i.e., the relaxation dynamics can be described by a biased Brownian motion along the charge transfer direction. The experimental findings are also qualitatively supported by theoretical calculations including restrained electrostatic potential (RESP) and hole-electron distribution analyses.By strategic design and synthesis of a new series of phosphonium salts (compounds 1-7[OTf]), where [OTf]- stands for the trifluoromethanesulfonate anion, we performed comprehensive spectroscopic and dynamic studies on the photoinduced anion migration in toluene. Our aim is to probe if the anion migration is associated with an intrinsic barrier or is barrier-free. After the occurrence of excited-state intramolecular charge transfer (ESICT) in 1-7, the charge redistribution of the cation triggers the translocation of the counter anion [OTf]-, resulting in emission spectral temporal evolution. As a result, we describe the photoinduced anion migration by introducing spectral response function C(t), a concept adopted from the solvent diffusional relaxation. The experimental results indicate that the anion migration lacks an intrinsic barrier, i.e., the relaxation dynamics can be described by a biased Brownian motion along the charge transfer direction. The experimental findings are also qualitatively supported by theoretical calculations including restrained electrostatic potential (RESP) and hole-electron distribution analyses.
By strategic design and synthesis of a new series of phosphonium salts (compounds 1–7[OTf]), where [OTf]− stands for the trifluoromethanesulfonate anion, we performed comprehensive spectroscopic and dynamic studies on the photoinduced anion migration in toluene. Our aim is to probe if the anion migration is associated with an intrinsic barrier or is barrier-free. After the occurrence of excited-state intramolecular charge transfer (ESICT) in 1–7, the charge redistribution of the cation triggers the translocation of the counter anion [OTf]−, resulting in emission spectral temporal evolution. As a result, we describe the photoinduced anion migration by introducing spectral response function C(t), a concept adopted from the solvent diffusional relaxation. The experimental results indicate that the anion migration lacks an intrinsic barrier, i.e., the relaxation dynamics can be described by a biased Brownian motion along the charge transfer direction. The experimental findings are also qualitatively supported by theoretical calculations including restrained electrostatic potential (RESP) and hole–electron distribution analyses. Compared to solvent relaxation in polar solvents, anion migration in toluene occurs at a much slower rate (C(t) analysis) and primarily involves translational motion of anion from the donor to the acceptor.
By strategic design and synthesis of a new series of phosphonium salts (compounds 1–7[OTf]), where [OTf]− stands for the trifluoromethanesulfonate anion, we performed comprehensive spectroscopic and dynamic studies on the photoinduced anion migration in toluene. Our aim is to probe if the anion migration is associated with an intrinsic barrier or is barrier-free. After the occurrence of excited-state intramolecular charge transfer (ESICT) in 1–7, the charge redistribution of the cation triggers the translocation of the counter anion [OTf]−, resulting in emission spectral temporal evolution. As a result, we describe the photoinduced anion migration by introducing spectral response function C ( t ), a concept adopted from the solvent diffusional relaxation. The experimental results indicate that the anion migration lacks an intrinsic barrier, i.e. , the relaxation dynamics can be described by a biased Brownian motion along the charge transfer direction. The experimental findings are also qualitatively supported by theoretical calculations including restrained electrostatic potential (RESP) and hole–electron distribution analyses.
By strategic design and synthesis of a new series of phosphonium salts (compounds 1-7[OTf]), where [OTf]- stands for the trifluoromethanesulfonate anion, we performed comprehensive spectroscopic and dynamic studies on the photoinduced anion migration in toluene. Our aim is to probe if the anion migration is associated with an intrinsic barrier or is barrier-free. After the occurrence of excited-state intramolecular charge transfer (ESICT) in 1-7, the charge redistribution of the cation triggers the translocation of the counter anion [OTf]-, resulting in emission spectral temporal evolution. As a result, we describe the photoinduced anion migration by introducing spectral response function C(t), a concept adopted from the solvent diffusional relaxation. The experimental results indicate that the anion migration lacks an intrinsic barrier, i.e., the relaxation dynamics can be described by a biased Brownian motion along the charge transfer direction. The experimental findings are also qualitatively supported by theoretical calculations including restrained electrostatic potential (RESP) and hole-electron distribution analyses.
By strategic design and synthesis of a new series of phosphonium salts (compounds 1-7[OTf] ), where [OTf] − stands for the trifluoromethanesulfonate anion, we performed comprehensive spectroscopic and dynamic studies on the photoinduced anion migration in toluene. Our aim is to probe if the anion migration is associated with an intrinsic barrier or is barrier-free. After the occurrence of excited-state intramolecular charge transfer (ESICT) in 1-7 , the charge redistribution of the cation triggers the translocation of the counter anion [OTf] − , resulting in emission spectral temporal evolution. As a result, we describe the photoinduced anion migration by introducing spectral response function C ( t ), a concept adopted from the solvent diffusional relaxation. The experimental results indicate that the anion migration lacks an intrinsic barrier, i.e. , the relaxation dynamics can be described by a biased Brownian motion along the charge transfer direction. The experimental findings are also qualitatively supported by theoretical calculations including restrained electrostatic potential (RESP) and hole-electron distribution analyses. Compared to solvent relaxation in polar solvents, anion migration in toluene occurs at a much slower rate ( C ( t ) analysis) and primarily involves translational motion of anion from the donor to the acceptor.
Author Koshevoy, Igor O
Partanen, Iida
Chang, Kai-Hsin
Lin, Yan-Ding
Chou, Pi-Tai
Qu, Hao-Ting
Belyaev, Andrey
AuthorAffiliation Department of Chemistry
National Taiwan University
University of Eastern Finland
Department of Chemistry/Nanoscience Center
University of Jyväskylä
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Author_xml – sequence: 1
  givenname: Hao-Ting
  surname: Qu
  fullname: Qu, Hao-Ting
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  givenname: Iida
  surname: Partanen
  fullname: Partanen, Iida
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  givenname: Kai-Hsin
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/39568931$$D View this record in MEDLINE/PubMed
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Issue 47
Keywords REACTION-RATES
NEGATIVE SOLVATOCHROMISM
SHUTTLING DYNAMICS
DONOR
SOLVATION DYNAMICS
ACCEPTOR BIPHENYLS
INTRAMOLECULAR CHARGE-TRANSFER
COUNTERION MIGRATION
ELECTRONIC-STRUCTURE
EXCITED-STATES
Language English
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For ESI and crystallographic data in CIF or other electronic format see DOI
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https://doi.org/10.1039/d4sc04738a
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Snippet By strategic design and synthesis of a new series of phosphonium salts (compounds 1-7[OTf] ), where [OTf] − stands for the trifluoromethanesulfonate anion, we...
By strategic design and synthesis of a new series of phosphonium salts (compounds 1–7[OTf]), where [OTf]− stands for the trifluoromethanesulfonate anion, we...
By strategic design and synthesis of a new series of phosphonium salts (compounds 1-7[OTf]), where [OTf]- stands for the trifluoromethanesulfonate anion, we...
By strategic design and synthesis of a new series of phosphonium salts (compounds 1-7[OTf]), where [OTf] stands for the trifluoromethanesulfonate anion, we...
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SubjectTerms Anions
Charge transfer
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Electron distribution
Excitation spectra
Ion migration
Physical Sciences
Response functions
Science & Technology
Spectral sensitivity
Toluene
Title Insights into the photoinduced anion translocation of donor-π-acceptor (ion) molecules
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