Cascaded Excited‐State Intramolecular Proton Transfer Towards Near‐Infrared Organic Lasers Beyond 850 nm

Wu, Junjie; Zhuo, Ming‐Peng; Lai, Runchen; Zou, Sheng‐Nan; Yan, Changcun; Yuan, Yi; Shen, Yang; Wei, Guiwu; Wang, Xue‐Dong; Liao, Liang‐Sheng

doi:10.1002/ange.202016786

Cited by 21 publications

(10 citation statements)

References 36 publications

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“…This is a typical behavior in multi‐component luminous systems [46] . In contrast, the dependency on the detection wavelengths gradually became very low as the temperature increased and seemed to be completely lost at 280 K. Such indistinguishable PL species have been described in some dual‐excimer, [30] intramolecular charge‐transfer, [47] and excited‐state intramolecular proton‐transfer [48, 49] systems, suggesting the attainment of thermal equilibrium of the two excited states. Under this situation, two types of radiative decay pathways were spectrally indistinguishable.…”

Section: Resultsmentioning

confidence: 90%

Alternately π‐Stacked Systems Assisted by o‐Carborane: Dual Excimer Emission and Color Modulation by B_cage‐Methylation

2022

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Herein, we report the unique solid‐state excimer emission of three types of acridine‐tethered o‐carboranes with variable degrees of methylation at the o‐carborane unit. They all showed columnar packing structures based on dimer formation, and two types of π‐overlapping motifs were alternately stacked. From the photoluminescence (PL) measurements on the crystalline samples, it was found that three types of luminescence bands can simultaneously appear: monomer emission, excimer emission from the moderately π‐stacked intra‐dimer unit, and excimer emission from the widely π‐stacked inter‐dimer unit. Consequently, the PL colors were drastically changed by the steric effect of the methyl groups, with a strong correlation found between the π‐overlapping and excimer character. In addition, variable‐temperature PL measurements revealed that these PL species should be in thermal equilibrium at room temperature, with the intensity ratios sensitive toward temperature changes.

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Section: Resultsmentioning

confidence: 90%

Alternately π‐Stacked Systems Assisted by o‐Carborane: Dual Excimer Emission and Color Modulation by B_cage‐Methylation

2022

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“…designed and synthesized an organic molecule ( E )‐1‐(1,8‐dihydroxynaphthalen‐2‐yl)‐3‐(4‐(dimethylamino)‐ 2‐methoxyphenyl)prop‐2‐en‐1‐one (DDMP, compound 8 ), which has two adjacent intramolecular hydrogen bonds and can perform excited state intramolecular double proton transfer (ESDPT). [ 116 ] The ESDPT process is shown in Figure 16a. The relative energies of the ground state S 0 and the first electronically excited state S 1 of the DDMP system were calculated in vacuum, as shown in Figure 16b.…”

Section: Esipt‐based Organic Nir Lasersmentioning

confidence: 99%

Organic Near‐Infrared Luminescent Materials Based on Excited State Intramolecular Proton Transfer Process^†

et al. 2022

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Organic near-infrared (NIR) luminescent materials have captured intense research interest owing to their potential applications in optical communication, data storage, bioimaging, sensing and night vision. Excited state intramolecular proton transfer (ESIPT) process with absorption in normal form while emission in tautomer form can lead to a distinct redshift emission, based on which, a lot of organic NIR luminescent materials were designed. Because of attractive features such as ultrahigh sensitivity to the surroundings, large Stokes shift, and inherent four level system, ESIPT based NIR luminescent materials are supposed to be ideal fluorescent probes and gain materials. In this review, first, organic near-infrared luminescent materials based on ESIPT process are summarized according to the core structures. Second, recent advances of ESIPT-based organic near-infrared fluorescent probes and organic NIR lasers are reviewed. Finally, the current challenges and prospects of ESIPT-based organic NIR luminescent materials are introduced.

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“…[13][14][15] Narrow bandgap organic compounds possess strong absorption and/or emission in near-infrared (NIR) region and are required for solar-energy-related applications, bio-imaging and medical applications. [16][17][18][19][20] Generally, organic molecules with narrow bandgaps can be designed by introducing of electron donating-accepting (D-A) structures and quinoid structures. 21,22 N-Type organic semiconductors are essential materials in OFETs and OSCs.…”

Section: Introductionmentioning

confidence: 99%

An n -Type All-Fused-Ring Molecule with Narrow Bandgap

Zhang

Miao

et al. 2023

CCS Chem

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All-fused-ring π-conjugated molecules have received great attention because of their unique electronic structures, low conformation disorder and excellent opto-electronic properties. Most of all-fused-ring molecules are p-type organic semiconductors and possess medium bandgaps. In this work, we design and synthesize an all-fused-ring molecule (FM1) with n-type property and narrow bandgap, which is a ten-fusedring system composing of one electron-deficient benzotriazole core, two electron-rich thienopyrrole bridging units and two electron-deficient malononitrile-functionalized end-cappers. FM1 exhibits low-lying HOMO/LUMO energy levels of −5.77 eV/−3.89 eV, high electron mobility of 6.0 × 10 −4 cm 2 V −1 s −1 , optical bandgap of 1.50 eV and maximum absorption wavelength of 769 nm. Because of the all-fused-ring skeleton, FM1 shows superior photo stability and chemical stability. We use FM1 as an electron acceptor and successfully construct organic solar cell (OSC) devices with a decent power conversion efficiency (PCE) of 10.8%. Most importantly, the intrinsic stability of FM1 leads to its excellent OSC device stability. After irradiation with simulated solar light for 16 hours, while control OSC device of the state-of-the-art small molecule electron acceptor shows 46% decrease of PCE, the unencapsulated OSC device of FM1 exhibits only 9% decrease of PCE.

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Cascaded Excited‐State Intramolecular Proton Transfer Towards Near‐Infrared Organic Lasers Beyond 850 nm

Cited by 21 publications

References 36 publications

Alternately π‐Stacked Systems Assisted by o‐Carborane: Dual Excimer Emission and Color Modulation by B_cage‐Methylation

Alternately π‐Stacked Systems Assisted by o‐Carborane: Dual Excimer Emission and Color Modulation by B_cage‐Methylation

Organic Near‐Infrared Luminescent Materials Based on Excited State Intramolecular Proton Transfer Process^†

An n -Type All-Fused-Ring Molecule with Narrow Bandgap

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Cascaded Excited‐State Intramolecular Proton Transfer Towards Near‐Infrared Organic Lasers Beyond 850 nm

Cited by 21 publications

References 36 publications

Alternately π‐Stacked Systems Assisted by o‐Carborane: Dual Excimer Emission and Color Modulation by Bcage‐Methylation

Alternately π‐Stacked Systems Assisted by o‐Carborane: Dual Excimer Emission and Color Modulation by Bcage‐Methylation

Organic Near‐Infrared Luminescent Materials Based on Excited State Intramolecular Proton Transfer Process†

An n -Type All-Fused-Ring Molecule with Narrow Bandgap

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Product

Resources

About

Alternately π‐Stacked Systems Assisted by o‐Carborane: Dual Excimer Emission and Color Modulation by B_cage‐Methylation

Alternately π‐Stacked Systems Assisted by o‐Carborane: Dual Excimer Emission and Color Modulation by B_cage‐Methylation

Organic Near‐Infrared Luminescent Materials Based on Excited State Intramolecular Proton Transfer Process^†