2,6-Bis(arylsulfonyl)anilines as Fluorescent Scaffolds through Intramolecular Hydrogen Bonds: Solid-State Fluorescence Materials and Turn-On-Type Probes Based on Aggregation-Induced Emission

ChemPlusChem ◽  
2014 ◽  
Vol 79 (4) ◽  
pp. 536-545 ◽  
Author(s):  
Teruo Beppu ◽  
So Kawata ◽  
Naoya Aizawa ◽  
Yong-Jin Pu ◽  
Yasuyuki Abe ◽  
...  
Keyword(s):  
Solid State ◽  
Hydrogen Bonds ◽  
Intramolecular Hydrogen Bonds ◽  
Aggregation Induced Emission ◽  
Turn On ◽  
Solid State Fluorescence ◽  
Intramolecular Hydrogen

scholarly journals A highly efficient solution and solid state ESIPT fluorophore and its OLEDs application

2021 ◽  
Author(s):  
Pei Yu ◽  
Virgile Trannoy ◽  
Anne Léaustic ◽  
Sophie Gadan ◽  
Régis Guillot ◽  
...  
Keyword(s):  
Excited State ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Dicarboxylic Acid ◽  
Ethyl Ester ◽  
Efficient Solution ◽  
Acid Ethyl Ester ◽  
Intramolecular Hydrogen Bonds ◽  
Highly Efficient ◽  
Intramolecular Hydrogen

We present herein the synthesis and the photophysics of 2,2’-bipyridine-3,3’-diol-5,5’-dicarboxylic acid ethyl ester (BP(OH)2DCEt2), an excited state intramolecular proton tranfer (ESIPT)-based fluorophore featuring two identical intramolecular hydrogen bonds. BP(OH)2DCEt2 emits...

scholarly journals Naphthazarin Derivatives in the Light of Intra- and Intermolecular Forces

Molecules ◽  
2021 ◽  
Vol 26 (18) ◽  
pp. 5642
Author(s):  
Karol Kułacz ◽  
Michał Pocheć ◽  
Aneta Jezierska ◽  
Jarosław J. Panek
Keyword(s):  
Perturbation Theory ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Proton Transfer ◽  
Gas Phase ◽  
Quantum Effects ◽  
Broad Absorption ◽  
Intramolecular Hydrogen Bonds ◽  
Intramolecular Hydrogen ◽  
Nuclear Quantum Effects

Our long-term investigations have been devoted the characterization of intramolecular hydrogen bonds in cyclic compounds. Our previous work covers naphthazarin, the parent compound of two systems discussed in the current work: 2,3-dimethylnaphthazarin (1) and 2,3-dimethoxy-6-methylnaphthazarin (2). Intramolecular hydrogen bonds and substituent effects in these compounds were analyzed on the basis of Density Functional Theory (DFT), Møller–Plesset second-order perturbation theory (MP2), Coupled Clusters with Singles and Doubles (CCSD) and Car-Parrinello Molecular Dynamics (CPMD). The simulations were carried out in the gas and crystalline phases. The nuclear quantum effects were incorporated a posteriori using the snapshots taken from ab initio trajectories. Further, they were used to solve a vibrational Schrödinger equation. The proton reaction path was studied using B3LYP, ωB97XD and PBE functionals with a 6-311++G(2d,2p) basis set. Two energy minima (deep and shallow) were found, indicating that the proton transfer phenomena could occur in the electronic ground state. Next, the electronic structure and topology were examined in the molecular and proton transferred (PT) forms. The Atoms In Molecules (AIM) theory was employed for this purpose. It was found that the hydrogen bond is stronger in the proton transferred (PT) forms. In order to estimate the dimers’ stabilization and forces responsible for it, the Symmetry-Adapted Perturbation Theory (SAPT) was applied. The energy decomposition revealed that dispersion is the primary factor stabilizing the dimeric forms and crystal structure of both compounds. The CPMD results showed that the proton transfer phenomena occurred in both studied compounds, as well as in both phases. In the case of compound 2, the proton transfer events are more frequent in the solid state, indicating an influence of the environmental effects on the bridged proton dynamics. Finally, the vibrational signatures were computed for both compounds using the CPMD trajectories. The Fourier transformation of the autocorrelation function of atomic velocity was applied to obtain the power spectra. The IR spectra show very broad absorption regions between 700 cm−1–1700 cm−1 and 2300 cm−1–3400 cm−1 in the gas phase and 600 cm−1–1800 cm−1 and 2200 cm−1–3400 cm−1 in the solid state for compound 1. The absorption regions for compound 2 were found as follows: 700 cm−1–1700 cm−1 and 2300 cm−1–3300 cm−1 for the gas phase and one broad absorption region in the solid state between 700 cm−1 and 3100 cm−1. The obtained spectroscopic features confirmed a strong mobility of the bridged protons. The inclusion of nuclear quantum effects showed a stronger delocalization of the bridged protons.

Controlling emissive properties by intramolecular hydrogen bonds: alkyl and aryl meso‐substituted porphycenes

2021 ◽  
Author(s):  
Jacek Waluk ◽  
Arkadiusz Listkowski ◽  
Natalia Masiera ◽  
Michał Kijak ◽  
Roman Luboradzki ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Intramolecular Hydrogen Bonds ◽  
Intramolecular Hydrogen

Energies of intramolecular hydrogen bonds in some alcohols

1974 ◽  
Vol 20 (3) ◽  
pp. 414-415
Author(s):  
Ya. A. Shuster ◽  
V. A. Granzhan ◽  
P. M. Zaitsev
Keyword(s):  
Hydrogen Bonds ◽  
Intramolecular Hydrogen Bonds ◽  
Intramolecular Hydrogen

Carbazole-modified thiazolo[3,2-c][1,3,5,2]oxadiazaborinines exhibiting aggregation-induced emission and mechanofluorochromism

2021 ◽  
Author(s):  
Mykhaylo A. Potopnyk ◽  
Mykola Kravets ◽  
Roman Luboradzki ◽  
Dmytro Volyniuk ◽  
Volodymyr Sashuk ◽  
...  
Keyword(s):  
Solid State ◽  
Fluorescence Properties ◽  
Aggregation Induced Emission ◽  
Donor Acceptor ◽  
Solid State Fluorescence ◽  
Active Donor

Two novel AIE-active donor–acceptor organoboron complexes with a carbazole donor unit are developed and their morphology-dependent solid-state fluorescence properties are established.

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