π–π Interactions: Influence on Molecular Packing and Solid‐State Emission of ESIPT and non‐ESIPT Motifs

Padalkar, Vikas S.; Sakamaki, Daisuke; Kuwada, Kenji; Horio, Akifumi; Okamoto, Haruka; Tohnai, Norimitsu; Akutagawa, Tomoyuki; Sakai, Keita; Seki, Shu

doi:10.1002/ajoc.201600159

Cited by 40 publications

(27 citation statements)

References 45 publications

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“…As reported in our earlier communications, solid/aggregated states could be achieved by suppressing non‐radiative pathways. Various donor (aromatic amines) and acceptor (azoles, triazoles, diazole) groups have been reported in the past .…”

Section: Introductionsupporting

confidence: 63%

AIE Active Carbazole-Benzothiazole Based ESIPT Motifs: Positional Isomers Directing the Optical and Electronic Properties

et al. 2017

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Three positional isomers based on carbazole (Cz) and hydroxy benzothiazole (HBT) were synthesized targeting solid state organic emitters by Suzuki coupling reaction and their optical, structural and electronic properties were compared. The changing of position of HBT unit on 9‐phenyl‐9H‐carbazole alters the optical and structural properties significantly. The synthesized compounds are highly emissive in solid and aggregated state (Φf=∼ 40 %) and weakly emissive in solvents of different polarities (Φf=2.6‐17 %). The difference in the fluorescence quantum efficiency among the positional isomers can be assigned to conformational differences which were further supported by geometrical parameters computed by DFT computations. The present Cz‐HBT based ESIPT motifs are endowed with aggregation induced emission (AIE), solid state and polarity sensitive emission with large Stokes shift.

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Section: Introductionsupporting

confidence: 63%

AIE Active Carbazole-Benzothiazole Based ESIPT Motifs: Positional Isomers Directing the Optical and Electronic Properties

et al. 2017

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“…Yamato et al . and Hariharan et al . have shown that strong π–stacking interactions can lead to extensive excimer formation in the solid state/thin films with a consequent reduction in the fluorescence quantum yield.…”

Section: Resultsmentioning

confidence: 99%

Exploration of the Luminescence Properties of Organic Phosphate Salts of 3‐Quinoline‐ and 5‐Isoquinolineboronic Acid

et al. 2019

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3-Quinoline-and 5-isoquinolineboronic acids (3QBA and 5IQBA) were combined with 1-naphthyl and diphenyl phosphate (1NP and DPP) to give three crystalline molecular salts of 1:1 stoichiometric composition, viz., 3QBA-1NP, 5IQBA-1NP and 3QBA-DPP. The products were characterized by elemental analysis, single-crystal X-ray diffraction studies, IR spectroscopy, luminescence spectroscopy and TG-DSC measurements. The analysis of the solid-state structures revealed that the molecular components are linked by strong charge-assisted hydrogen bonds forming heterodimeric synthons of the type B(OH) 2 ··· -O 2 P and N + -H···O(P). In addition, the hydrogen phos- [a] Crystalline solids of compounds 3QBA-1NP, 5IQBA-1NP and 3QBA-DPP were isolated upon combination of the starting reagents in absolute ethanol. The products were characterized by elemental analysis, single-crystal X-ray diffraction (SCXRD) analysis, IR spectroscopy and TG-DSC analysis. In addition, the luminescence properties were explored. 2708 Scheme 1. List of compounds employed for the formation of the molecular salts described in this contribution.

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“…The quenching of fluorescence can be attributed to the supramolecular arrangement of (I) in the crystal structure that involves one of the cyanophenyl rings in weak face-to-facedisplacedinteractions [centroid-centroid distance = 4.54 Å , slippage = 2.96 Å and dihedral angle between planes = 0.0 ] (Fig. 3) (Kupcewicz & Małecka, 2015;He et al 2015;Padalkar et al, 2016).…”

Section: Figurementioning

confidence: 99%

Supramolecular arrangement and photophysical properties of a dinuclear cyanophenylboronic acid ester

et al. 2018

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Boronic esters are useful building blocks for crystal engineering and the generation of supramolecular architectures, including macrocycles, cages and polymers (one-, two-and three-dimensional), with potential utility in diverse fields such as separation, storage and luminescent materials. The novel dinuclear cyanophenylboronic ester described herein, namely 4,4 0 -(2,4,8,10-tetraoxa-3,9diboraspiro[5.5]undecane-3,9-diyl)dibenzonitrile, C 19 H 16 B 2 N 2 O 4 , was prepared by condensation of 4-cyanophenylboronic acid and pentaerythritol and fully characterized by elemental analysis, IR and NMR ( 1 H and 11 B) spectroscopy, single-crystal X-ray diffraction analysis and TG-DSC (thermogravimetrydifferential scanning calorimetry) studies. In addition, the photophysical properties were examined in solution and in the solid state by UV-Vis and fluorescence spectroscopies. Density functional theory (DFT) calculations with ethanol as solvent reproduced reasonably well the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) of the title compound. Hirshfeld surface and fingerprint plot analyses are presented to illustrate the supramolecular connectivity in the solid state.

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π–π Interactions: Influence on Molecular Packing and Solid‐State Emission of ESIPT and non‐ESIPT Motifs

Cited by 40 publications

References 45 publications

AIE Active Carbazole-Benzothiazole Based ESIPT Motifs: Positional Isomers Directing the Optical and Electronic Properties

AIE Active Carbazole-Benzothiazole Based ESIPT Motifs: Positional Isomers Directing the Optical and Electronic Properties

Exploration of the Luminescence Properties of Organic Phosphate Salts of 3‐Quinoline‐ and 5‐Isoquinolineboronic Acid

Supramolecular arrangement and photophysical properties of a dinuclear cyanophenylboronic acid ester

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