A metal-lustrous porphyrin foil

Morisue, Mitsuhiko; Hoshino, Yuki; Shimizu, Masaki; Tomita, Shogo; Sasaki, Sono; Sakurai, Shinichi; Hikima, Takaaki; Kawamura, Ayaka; Kohri, Michinari; Matsui, Jun; Yamao, Takeshi

doi:10.1039/c7cc06159e

Cited by 20 publications

(24 citation statements)

References 46 publications

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“…In the porphyrin foil, 1 adopted a form of amorphous phase at room temperature. 28 The porphyrin foil exhibited emission at 1138 and 950 nm ( Figure 7 ). In this case, the considerable overlap of intense absorption of the porphyrin foil should distort the spectral shape in the wavelength region shorter than the Q band and the normal emission should partly emerge at 950 nm, although the SWIR emission longer than the Q band should also be transmitted.…”

Section: Resultsmentioning

confidence: 99%

“… Emission–excitation contour map of the porphyrin foil. Excitation spectrum monitored at 1000 nm (black line), absorption spectrum obtained by spectroscopic ellipsometry (gray line, adapted from ref ( 28 )) (left panel), and emission spectra obtained by excitation at 470 and 800 nm (upper panel). It should be noticed that no emission at 827 nm was found.…”

Section: Resultsmentioning

confidence: 99%

“… WAXD profile of the porphyrin foil (red line, adapted from ref ( 28 )) and GIWAXD profile of the spin-cast film of the porphyrin array on a silicon wafer (blue line) after background correction (A), where representative peaks are shown as d -spacing ( d = 2π/ q ). The observed GIWAXD pattern (B) and azimuthal-angle dependence of the intensity of the primary GIWAXD peak at the magnitude of the scattering vector, q , of approximately 2.1 nm –1 (C).…”

Section: Resultsmentioning

confidence: 99%

“…Synthesis of polymer 1 was described in our previous report. 28 Model compound 2 was newly synthesized.…”

Section: Experimental Sectionmentioning

confidence: 99%

“… 23 − 26 The porphyrin glass is highly resistant to crystallization and is tolerant of expansion of the π-system through supramolecular and covalent polymerization. 27 , 28 In principle, the amorphous or glass phase is kinetically constrained from crystallization and incorporates a free volume in the frozen liquid by losing macroscopic fluidity. Thus, the free volume allows some extent of microscopic conformational fluctuation in the photoexcited state, leading to excimer formation.…”

Section: Introductionmentioning

confidence: 99%

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Fully Conjugated Porphyrin Glass: Collective Light-Harvesting Antenna for Near-Infrared Fluorescence beyond 1 μm

et al. 2018

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Expanded π-systems with a narrow highest occupied molecular orbital–lowest unoccupied molecular orbital band gap encounter deactivation of excitons due to the “energy gap law” and undesired aggregation. This dilemma generally thwarts the near-infrared (NIR) luminescence of organic π-systems. A sophisticated cofacially stacked π-system is known to involve exponentially tailed disorder, which displays exceptionally red-shifted fluorescence even as only a marginal emission component. Enhancement of the tail-state fluorescence might be advantageous to achieve NIR photoluminescence with an expected collective light-harvesting antenna effect as follows: (i) efficient light-harvesting capacity due to intense electronic absorption, (ii) a long-distance exciton migration into the tail state based on a high spatial density of the chromophore site, and (iii) substantial transmission of NIR emission to circumvent the inner filter effect. Suppression of aggregation-induced quenching of fluorescence could realize collective light-harvesting antenna for NIR-luminescence materials. This study discloses an enhanced tail-state NIR fluorescence of a self-standing porphyrin film at 1138 nm with a moderate quantum efficiency based on a fully π-conjugated porphyrin that adopts an amorphous form, called “porphyrin glass”.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…Synthesis of polymer 1 was described in our previous report. 28 Model compound 2 was newly synthesized.…”

Section: Experimental Sectionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Fully Conjugated Porphyrin Glass: Collective Light-Harvesting Antenna for Near-Infrared Fluorescence beyond 1 μm

et al. 2018

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Perfluorophenyl‐Directed Giant Porphyrin J‐Aggregates

Morisue

Ueno

Muraoka

et al. 2019

Chemistry A European J

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Quadrupolar interactions of porphyrin bearing two pentafluorophenylethynyl terminals (1) drove the formation of a successive one‐dimensional staircase structure, i.e., J‐aggregates, to yield millimeter‐length needles with a single‐crystalline character in methylcyclohexane solution. In contrast, π‐stacked interactions of porphyrin bearing two nonfluorinated phenyl terminals (2) formed no aggregates in solution. A spin‐cast film of 1 also showed bathochromic shift of the Soret and Q bands, indicating the formation of J‐aggregates. The molecular arrangement of the J‐aggregates was revealed by microbeam glazing‐incidence wide‐angle X‐ray diffraction (GIWAXD), and was in good agreement with the optimized structure generated by density functional theory (DFT) calculations.

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An elaborate route of exclusive sonogashira polycondensation to alternating BODIPY–porphyrin ethynylene‐conjugated polymer

Morisue

Kawanishi

Nakano

2019

J. Polym. Sci. Part A: Polym. Chem.

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The first synthesis of the fully conjugated ethynylene‐linked polymer incorporating boron dipyrrine complex (BODIPY) and zinc porphyrin in the main chain was performed based on the exclusive Sonogashira polycondensation. Comprehensive experimental and theoretical investigations lead to an elaborate synthetic route to circumvent the possible side reactions of BODIPY in the presence of the palladium catalyst. Additionally, optimization of the synthetic conditions found that dichloromethane as the solvent suppresses the formation of the pseudo‐trans dimer of the copper acetylide and mitigates the undesired oxidative homocoupling reaction. Eventually, the exclusive Sonogashira polycondensation in dichloromethane provided the alternating BODIPY–porphyrin ethynylene‐conjugated polymer, which displayed absorption up to the near‐infrared wavelengths. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 2457–2465

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A metal-lustrous porphyrin foil

Cited by 20 publications

References 46 publications

Fully Conjugated Porphyrin Glass: Collective Light-Harvesting Antenna for Near-Infrared Fluorescence beyond 1 μm

Fully Conjugated Porphyrin Glass: Collective Light-Harvesting Antenna for Near-Infrared Fluorescence beyond 1 μm

Perfluorophenyl‐Directed Giant Porphyrin J‐Aggregates

An elaborate route of exclusive sonogashira polycondensation to alternating BODIPY–porphyrin ethynylene‐conjugated polymer

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