Stabilizing g-States in Centrosymmetric Tetrapyrroles: Two-Photon-Absorbing Porphyrins with Bright Phosphorescence

Esipova, Tatiana V.; Rivera-Jacquez, Héctor J.; Weber, Bruno; Masunov, Artëm E.; Vinogradov, Sergei A.

doi:10.1021/acs.jpca.7b04333

Stabilizing g-States in Centrosymmetric Tetrapyrroles: Two-Photon-Absorbing Porphyrins with Bright Phosphorescence

Journal Article · Wed Aug 02 00:00:00 EDT 2017 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

DOI:https://doi.org/10.1021/acs.jpca.7b04333· OSTI ID:1480255

Esipova, Tatiana V. ^[1]; ^[2]; Weber, Bruno ^[3]; ^[4]; ^[1]

Univ. of Pennsylvania, Philadelphia, PA (United States)
Univ. of Central Florida, Orlando, FL (United States)
Univ. of Zurich (Switzerland)
Univ. of Central Florida, Orlando, FL (United States); Russian Academy of Sciences (RAS), Moscow (Russian Federation); South Ural State Univ., Chelyabinsk (Russia); National Nuclear Research Univ. MEPhI, Moscow (Russia)

With time-dependent density functional theory (TDDFT) and sum-overstates (SOS) formalism, we predicted significant stabilization of 2P-active g-states in a compact fully symmetric porphyrin, in which all four pyrrolic fragments are fused with phathalimide residues via the β-carbon positions. The synthesis of a soluble, nonaggregating meso-unsubstituted tetraarylphthalimidoporphyrin (TAPIP) was then developed, and the spectroscopic measurements confirmed that a strongly 2P-active state in this porphyrin is stabilized below the B (Soret) state level. Single-crystal X-ray analysis revealed near-ideally planar geometry of the TAPIP macrocycle, while its tetra-meso-arylated analogue (meso-Ar₄TAPIP) was found to be highly saddled. Consistent with these structural features, Pt meso-Ar4TAPIP phosphoresces rather weakly (Φ_phos = 0.05 in DMF at 22 °C), while both Pt and Pd complexes of TAPIP are highly phosphorescent (Φ_phos = 0.45 and 0.23, respectively). Furthermore, PdTAPIP exhibits non-negligible thermally activated (E-type) delayed fluorescence (Φ_fl(d) ~ 0.012). Taken together, these photophysical properties make metal complexes of meso-unsubstituted tetaarylphthalimidoporphyrins the brightest 2P-absorbing phosphorescent chromophores known to date.

View Accepted Manuscript (DOE)

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC)

Sponsoring Organization:: National Institutes of Health (NIH); National Science Foundation (NSF); Swiss National Science Foundation; USDOE

OSTI ID:: 1480255

Journal Information:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory, Journal Name: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory Journal Issue: 33 Vol. 121; ISSN 1089-5639

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Theory and computations of two-photon absorbing photochromic chromophores Masunov, Artem E.; Mikhailov, Ivan A. European Journal of Chemistry, Vol. 1, Issue 2 https://doi.org/10.5155/eurjchem.1.2.142-161.119	journal	June 2010
Mapping oxygen concentration in the awake mouse brain Lyons, Declan G.; Parpaleix, Alexandre; Roche, Morgane eLife, Vol. 5 https://doi.org/10.7554/eLife.12024	journal	February 2016

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