Two-Photon Absorbing Phosphorescent Metalloporphyrins: Effects of $\pi$-Extension and Peripheral Substitution

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

doi:10.1021/jacs.6b09157

Title: Two-Photon Absorbing Phosphorescent Metalloporphyrins: Effects of $$\pi$$-Extension and Peripheral Substitution

Journal Article · Mon Nov 07 00:00:00 EST 2016 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.6b09157· OSTI ID:1488930

Esipova, Tatiana V. ^[1]; Rivera-Jacquez, Héctor J. ^[2]; Weber, Bruno ^[3]; Masunov, Artëm E. ^[4]; Vinogradov, Sergei A. ^[1]

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

The ability to form triplet excited states upon two-photon excitation is important for several applications of metalloporphyrins, including two-photon phosphorescence lifetime microscopy (2PLM) and two-photon photodynamic therapy (PDT). We analyzed one-photon (1P) and degenerate two-photon (2P) absorption properties of several phosphorescent Pt (II) porphyrins, focusing on the effects of aromatic π-extension and peripheral substitution on triplet emissivity and two-photon absorption (2PA). Our 2PA measurements for the first time made use of direct time-resolved detection of phosphorescence, having the ability to efficiently reject laser background through microsecond time gating. π-Extension of the porphyrin macrocycle by way of syn-fusion with two external aromatic fragments, such as in syn-dibenzo- (DBP) and syn-dinaphthoporphyrins (DNP), lowers the symmetry of the porphyrin skeleton. As a result, DBPs and DNPs exhibit stronger 2PA into the one-photon-allowed B (Soret) and Q states than fully symmetric (D_4h) nonextended porphyrins. However, much more 2P-active states lie above the B state and cannot be accessed due to the interfering linear absorption. Alkoxycarbonyl groups (CO₂R) in the benzo-rings dramatically enhance 2PA near the B state level. Time-dependent density functional theory (TDDFT) calculations in combinations with the sum-over-states (SOS) formalism revealed that the enhancement is due to the stabilization of higher-lying 2P-active states, which are dominated by the excitations involving orbitals extending onto the carbonyl groups. Furthermore, calculations predicted even stronger stabilization of the 2P-allowed gerade-states in symmetric Pt octaalkoxycarbonyl-tetrabenzoporphyrins. Experiments confirmed that the 2PA cross-section of PtTBP(CO₂Bu)₈ near 810 nm reaches above 500 GM in spite of its completely centrosymmetric structure. Combined with exceptionally bright phosphorescence (Φ_phos = 0.45), strong 2PA makes Pt(II) complexes of π-extended porphyrins a valuable class of chromophores for 2P applications. Another important advantage of these porphyrinoids is their compact size and easily scalable synthesis.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC); Univ. of Pennsylvania, Philadelphia, PA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Advanced Scientific Computing Research (ASCR); National Institutes of Health (NIH); National Science Foundation (NSF); Swiss National Science Foundation (SNSF); Russian Science Foundation; Russian Federation

Grant/Contract Number:: EB018464; NS092986; GM103591; DMR11-20901; 14-43-00052; 02.A03.21.0011

OSTI ID:: 1488930

Journal Information:: Journal of the American Chemical Society, Vol. 138, Issue 48; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 52 works

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