Multi‐Directional Mechanofluorochromism of Acetyl Pyrenes and Pyrenyl Ynones

Hirai, Yuichi; Laize-Générat, Lucie; Wrona-Piotrowicz, Anna; Makal, Anna; Brosseau, Arnaud; Michely, Laurent; Versace, Davy‐Louis; Allain, Clémence; Métivier, Rémi

doi:10.1002/cphc.202100294

Cited by 9 publications

(15 citation statements)

References 33 publications

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“…S1, ESI † ). 16 An increased broad emission band ( λ em3 ∼ 460 nm) and accompanying near-ultraviolet (UV) shoulder bands ( λ em1 ∼ 388 nm) with different degrees of contribution were observed ( Fig. 2 , blue lines).…”

Section: Resultsmentioning

confidence: 94%

“…This corroborates the purple-to-blue bathochromic MFC behaviours of Me 3 , Me 2 Et, and Et 3 , where the monomer-like conformation shifts to a dimer-/aggregated-like conformation under mechanical stimuli. 16 However, the similar values of atomic contacts between adjacent molecular surfaces and packing motifs still do not explain the distinct kinetic gap in the self-recovery processes that spontaneously occur after unloading. An energy framework analysis was also performed using CrystalExplorer to quantitatively visualise the topology of the intermolecular interactions in these crystals.…”

Section: Resultsmentioning

confidence: 98%

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Mechanofluorochromism and self-recovery of alkylsilylpyrene-1-carboxamides

Hirai,

Wrona-Piotrowicz,

Zakrzewski

et al. 2024

J. Mater. Chem. C

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Section: Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 98%

Mechanofluorochromism and self-recovery of alkylsilylpyrene-1-carboxamides

Hirai,

Wrona-Piotrowicz,

Zakrzewski

et al. 2024

J. Mater. Chem. C

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“…106 By conjugating three twisted motifs (2TPAN-TPA, Figures 2b inset and 3), Zhang et al achieved the first MRL system with more than three emission colors. 107 The slideable and compressible crystal structure with large void volume corroborates the relatively homogeneous and gradually In addition to the mechanical response of the individual molecules induced by the rotatable "paddles (or blades)" in specific arrangements (Figure 2b), 114 the packing motif (Figure 2c) 115,116 significantly affects the mechanical response of the materials. The speculated emission wavelengths before and after stimulation typically fit within the PL range of a single crystal (highest order) to that of a molten solid (lowest order).…”

Section: Molecular Design For Mrlmentioning

confidence: 58%

On Sense and Deform: Molecular Luminescence for Mechanoscience

Hirai

2024

ACS Appl. Opt. Mater.

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Mechanoscientific research fields encompassing chemistry, physics, and biology have advanced significantly over the last two decades. Notably, the study of photon-emitting phenomena in molecular solids responsive to mechanical stimulation is known as mechanoresponsive luminescence (MRL) and mechanoluminescence (ML). These phenomena exhibit significant potential for applications such as sensor technology and anti-counterfeiting measures. The versatility observed in molecular designs, enabling control over responsive thresholds and wavelengths, coupled with diverse mechanisms for inducing deformation, such as heat, light, and sound, significantly broadens the domain of mechanically sensitive molecular materials. However, the understanding of the nanomechanical aspects about these molecular solids remains elusive. A comprehensive examination of the interplay among molecular structures, deformation characteristics, and luminescence responses is essential for further exploration. Such insights are crucial for addressing the intrinsic limitation of “one-time use” associated with deformation-induced properties, necessitating a focus on solid-state healing processes as well. Recent investigations into inorganic-based ML systems applied to free-standing light sources and mechanical metamaterial design foreshadow the future trajectory of molecular-based systems. These advancements aim to facilitate the secondary use of generated photons and the efficient capture/transfer of mechanical cues, enhancing optical output. Molecular luminescence stands poised to make substantial contributions to the ongoing rapid progress in mechanoscience due to an expanding synthetic repertoire, heightened biocompatibility, and precise “structural control” at molecular and macroscopic scales.

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“…Mechanofluorochromic materials, which are solid organic light-emitting materials that change their luminous color upon mechanical stimuli by crushing or grinding, have attracted attention for their applications in security inks, memory chips, and pressure sensors [ 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 ]. Numerous organic mechanofluorochromic materials have been reported, including metal complexes [ 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 ], anthracene derivatives [ 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 ], pyrene derivatives [ 66 , 67 , 68 , 69 , 70 ,…”

Section: Introductionmentioning

confidence: 99%

Mechanofluorochromic Properties of 1,4-Diphenylanthracene Derivatives with Hypsochromic Shift

Kannen,

Adachi,

Nishimura

et al. 2024

Molecules

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Several types of 1,4-diphenylanthracene derivatives 1–4 were prepared, and their photophysical properties were observed in the solid and solution states. Interestingly, the CN-group-substituted 1,4-diphenylanthracene derivative 2 was found to exhibit a higher fluorescence quantum yield (ϕf = 0.71) in the solid state than in the solution state, probably due to the formation of an intermolecular Ar–CN⋯H–Ar hydrogen bond and antiparallel type locked packing structure in the solid state. Furthermore, for some derivatives, an increase in the fluorescence quantum yield was observed in the PMMA film (1 wt%) over both the solid state and the solution state. More interestingly, some of the 1,4-diphenylanthracene derivatives exhibited unusual mechanofluorochromic properties with a “hypsochromic shift” in luminous color depending on the substituents of the phenyl group, and with the derivatives having CF3, OMe, CN, and two F substituents (1d–1f, 2–4) showing a significant luminous color change with a “hypsochromic shift” after grinding. However, no change in the luminous color was observed for the derivatives having H, Me, and one F substituent (1a–1c), and especially for some of the CN-substituted derivatives, a reversible luminous color change with a “hypsochromic shift” was observed, probably due to the formation of an antiparallel type packing structure. These “hypsochromic” anthracene derivatives could probably be utilized as new mechanofluorochromic materials.

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Multi‐Directional Mechanofluorochromism of Acetyl Pyrenes and Pyrenyl Ynones

Cited by 9 publications

References 33 publications

Mechanofluorochromism and self-recovery of alkylsilylpyrene-1-carboxamides

Mechanofluorochromism and self-recovery of alkylsilylpyrene-1-carboxamides

On Sense and Deform: Molecular Luminescence for Mechanoscience

Mechanofluorochromic Properties of 1,4-Diphenylanthracene Derivatives with Hypsochromic Shift

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