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Title: Positional Effects from σ-Bonded Platinum(II) on Intersystem Crossing Rates in Perylenediimide Complexes: Synthesis, Structures, and Photophysical Properties

Abstract

In this research, the synthesis and photophysical properties of a series of new chromophores featuring Pt(II) σ-bonded to perylenediimide (PDI) cores are reported. A Pt(PPh3)2X (X = Cl, Br) moiety was attached to PDI in either the ortho or the bay position (2- or 1-positions respectively) or a Pt(PPh3)2 subunit was used to bridge two bay positions (1- and 12-positions) forming a Pt(II) cyclometalate. Through a combination of steady-state and transient absorption and photoluminescence spectroscopy, the excited-state dynamics of these molecules were revealed, indicating that the Pt atom location on the PDI has a substantial impact on observed intersystem crossing (ISC) rates. The ISC time constants for the bay-substituted and cyclometalated PDIs are between 2.67 and 1.29 ns, respectively, determined by the singlet fluorescence decays from the initially populated singlet excited states. In the case of the ortho-substituted PDI, ISC to the triplet state occurs on the ultrafast time scale with a time constant of 345 fs, determined through ultrafast transient absorption spectroscopy. In all examples, the measured PDI-based fluorescence quantum yields quantitatively correlate with the measured ISC rates leaving little doubt that variation in the Pt(II) substitution position(s) markedly influence the resultant photophysics. Electronic structure calculations suggest differing amountsmore » of metal-based contributions in the lowest excited states as a function of substitution position, supporting the trend of the observed ISC rates.« less

Authors:
 [1];  [2];  [3]; ORCiD logo [4]; ORCiD logo [5]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [6]; ORCiD logo [2]
+ Show Author Affiliations
  1. North Carolina State Univ., Raleigh, NC (United States)
  2. Georgia Inst. of Technology, Atlanta, GA (United States)
  3. National Research Centre, Moscow (Russian Federation). Kurchatov Institute
  4. New Mexico Highlands Univ., Las Vegas, NM (United States); Peoples’ Friendship Univ. of Russia (RUDN Univ.), Moscow (Russian Federation)
  5. New Mexico Highlands Univ., Las Vegas, NM (United States)
  6. Univ. of Kentucky, Lexington, KY (United States)
Publication Date:
Research Org.:
North Carolina State University, Raleigh, NC (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division; US Department of the Navy, Office of Naval Research (ONR); National Science Foundation (NSF); US Air Force Office of Scientific Research (AFOSR)
OSTI Identifier:
1633634
Grant/Contract Number:  
SC0011979; N00014-16-1-2985; DMR-1523611; FA9550-10-1-0558
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Physical Chemistry. C
Additional Journal Information:
Journal Volume: 122; Journal Issue: 25; Journal ID: ISSN 1932-7447
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
14 SOLAR ENERGY

Citation Formats

Yarnell, James E., Davydenko, Iryna, Dorovatovskii, Pavel V., Khrustalev, Victor N., Timofeeva, Tatiana V., Castellano, Felix N., Marder, Seth R., Risko, Chad, and Barlow, Stephen. Positional Effects from σ-Bonded Platinum(II) on Intersystem Crossing Rates in Perylenediimide Complexes: Synthesis, Structures, and Photophysical Properties. United States: N. p., 2018. Web. doi:10.1021/acs.jpcc.8b01003.
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Yarnell, James E., Davydenko, Iryna, Dorovatovskii, Pavel V., Khrustalev, Victor N., Timofeeva, Tatiana V., Castellano, Felix N., Marder, Seth R., Risko, Chad, & Barlow, Stephen. Positional Effects from σ-Bonded Platinum(II) on Intersystem Crossing Rates in Perylenediimide Complexes: Synthesis, Structures, and Photophysical Properties. United States. https://doi.org/10.1021/acs.jpcc.8b01003
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Yarnell, James E., Davydenko, Iryna, Dorovatovskii, Pavel V., Khrustalev, Victor N., Timofeeva, Tatiana V., Castellano, Felix N., Marder, Seth R., Risko, Chad, and Barlow, Stephen. Fri . "Positional Effects from σ-Bonded Platinum(II) on Intersystem Crossing Rates in Perylenediimide Complexes: Synthesis, Structures, and Photophysical Properties". United States. https://doi.org/10.1021/acs.jpcc.8b01003. https://www.osti.gov/servlets/purl/1633634.
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@article{osti_1633634,
title = {Positional Effects from σ-Bonded Platinum(II) on Intersystem Crossing Rates in Perylenediimide Complexes: Synthesis, Structures, and Photophysical Properties},
author = {Yarnell, James E. and Davydenko, Iryna and Dorovatovskii, Pavel V. and Khrustalev, Victor N. and Timofeeva, Tatiana V. and Castellano, Felix N. and Marder, Seth R. and Risko, Chad and Barlow, Stephen},
abstractNote = {In this research, the synthesis and photophysical properties of a series of new chromophores featuring Pt(II) σ-bonded to perylenediimide (PDI) cores are reported. A Pt(PPh3)2X (X = Cl, Br) moiety was attached to PDI in either the ortho or the bay position (2- or 1-positions respectively) or a Pt(PPh3)2 subunit was used to bridge two bay positions (1- and 12-positions) forming a Pt(II) cyclometalate. Through a combination of steady-state and transient absorption and photoluminescence spectroscopy, the excited-state dynamics of these molecules were revealed, indicating that the Pt atom location on the PDI has a substantial impact on observed intersystem crossing (ISC) rates. The ISC time constants for the bay-substituted and cyclometalated PDIs are between 2.67 and 1.29 ns, respectively, determined by the singlet fluorescence decays from the initially populated singlet excited states. In the case of the ortho-substituted PDI, ISC to the triplet state occurs on the ultrafast time scale with a time constant of 345 fs, determined through ultrafast transient absorption spectroscopy. In all examples, the measured PDI-based fluorescence quantum yields quantitatively correlate with the measured ISC rates leaving little doubt that variation in the Pt(II) substitution position(s) markedly influence the resultant photophysics. Electronic structure calculations suggest differing amounts of metal-based contributions in the lowest excited states as a function of substitution position, supporting the trend of the observed ISC rates.},
doi = {10.1021/acs.jpcc.8b01003},
journal = {Journal of Physical Chemistry. C},
number = 25,
volume = 122,
place = {United States},
year = {Fri Feb 23 00:00:00 EST 2018},
month = {Fri Feb 23 00:00:00 EST 2018}
}
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https://doi.org/10.1021/acs.jpcc.8b01003
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Cited by: 15 works
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Figures / Tables:

Chart 1 Chart 1: Pd(II) and Pt(II) PDI Derivatives and Numbering of the PDI Core
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Formation of Phenylene Oligomers Using Platinum−Phosphine Complexes
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  • Organometallics, Vol. 20, Issue 13
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Generation of (η2-benzyne)bis(triphenylphosphine)platinum(>0>): orthometallation of the Pt(PPh3)2 complexes of benzyne (C6H4 ) and cyclohexyne (C6H8)
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A novel reactivity in the reaction of cycloheptatetraene with Pt(PPh3)3
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Über die reduktive Eliminierung des Biphenyl-Systems aus substituiertentrans-Diphenylbis(triphenylphosphan)platin(II)-Verbindungen
journal, December 1982

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  • Chemische Berichte, Vol. 115, Issue 12
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Chiral platinum(II) complexes. Crystal and molecular structures of cis-[PtPhCl((R,R)-CHIRAPHOS)] and cis-[PtCl2((R,R)-CHIRAPHOS)]
journal, May 2001

Synthesis and Structure of Platinum Bis(phospholane) Complexes Pt(diphos*)(R)(X), Catalyst Precursors for Asymmetric Phosphine Alkylation
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Natural transition orbitals
journal, March 2003

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Quantum Yields for the Photosensitized Formation of the Lowest Electronically Excited Singlet State of Molecular Oxygen in Solution
journal, January 1993

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    Works referencing / citing this record:

    Long-lived triplet excited state in a platinum( ii ) perylene monoimide complex
    journal, January 2018

    • Yarnell, James E.; Chakraborty, Arnab; Myahkostupov, Mykhaylo
    • Dalton Transactions, Vol. 47, Issue 42
    • DOI: 10.1039/c8dt02496k

    Perylene Bisimide Dyes with up to Five Independently Introduced Substituents: Controlling the Functionalization Pattern and Photophysical Properties Using Regiospecific Bay Substitution
    journal, July 2019

    • Dubey, Rajeev K.; Eustace, Stephen J.; van Mullem, Jesse S.
    • The Journal of Organic Chemistry, Vol. 84, Issue 15
    • DOI: 10.1021/acs.joc.9b01131
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