Structure, spectroscopy, and theory calculations on 1,3-bis((5,6-dimethyl-1H-benzo[d]imidazol-1-yl)methyl)benzene

Li, Guangyue; Geng, Jian‐Chen; He, C.; Cui, Guang‐Hua

doi:10.1016/j.molstruc.2012.07.014

Cited by 14 publications

(2 citation statements)

References 40 publications

(31 reference statements)

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“…Furthermore, we also calculate the corresponding potential energy curves as shown in Figure . The potential energy curve of S 0 state is based on the shortening of F and H atom of hydroxyl from 2.30 Å to 1.00 Å with fixing the step of 0.05 Å, which has been confirm to be a good manner to deal with the studies of protonated and deprotonated processes . It can be seen clearly that the potential energy curve almost decreases along with the shortening H‐F bond length.…”

Section: Resultsmentioning

confidence: 89%

The revelation of ESIPT behavior and fluoride response mechanism for (E)‐2‐(((1H‐benzo[d]imidazol‐2‐yl)‐imino)methyl)‐5‐(dimethylamino)‐phenol

Zheng

Zhang

et al. 2019

J of Physical Organic Chem

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Given the tremendous potential of fluorescence sensors in recent years, in this work, as a kind of novel and few studied sensor containing both NH and OH binding sites, (E)-2- (((1H-benzo[d]imidazol-2-yl)-imino)methyl)-5-(dimethylamino)-phenol (bip) has been investigated on the excited state intramolecular proton transfer (ESIPT) based on time-dependent density functional theory (TDDFT) method. Our simulated absorption and fluorescence spectra based on the TDDFT method are in agreement with the experimental results.Two kinds of bip structures could found in the S 1 state, which could be attributed to the ESIPT reaction. Hydrogen bond strengthening has been testified in the S 1 state based on comparing staple bond lengths and bond angles involved in hydrogen bond between S 0 and S 1 states. The calculated infrared (IR) vibrational spectra at the O-H stretching vibrational region and theoretical hydrogen bonding energy also declare the phenomenon of hydrogen bond strengthening. The frontier molecular orbitals (MOs) analysis and Natural bond orbital (NBO) manifest the intramolecular charge transfer (ICT) characteristic for bip chromophore, which reveals the tendency of proton transfer.The potential energy curvess of the S 0 and S 1 states are constructed to explain the mechanism of the proton transfer in excited state in detail. Further, given fluorescence sensing mechanism, we present the addition of fluoride anion can spontaneously capture the hydrogen proton of hydroxyl forming intermolecular hydrogen bond O-H···F, which results in the formation of anion product with response fluoride anion.

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Section: Resultsmentioning

confidence: 89%

The revelation of ESIPT behavior and fluoride response mechanism for (E)‐2‐(((1H‐benzo[d]imidazol‐2‐yl)‐imino)methyl)‐5‐(dimethylamino)‐phenol

Zheng

Zhang

et al. 2019

J of Physical Organic Chem

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“…The constructing potential energy curve of S 0 state is based on the shortening of F and Si bond length from 5.00 to 1.40 Å with fixing the step of 0.10 Å, which is a good manner to deal with the studies of fluorescence sensor. [ 37–45 ] It can be seen clearly that the formation of the intermediate (i.e., the complex between TBDI and fluoride anion) is endergonic about 7.613 kcal/mol in the ground state. And the fluoride anion interacts with TBDI sensor via hydrogen bonding interaction in the intermediate complex.…”

Section: Resultsmentioning

confidence: 99%

Sensing of fluoride anion based on desilylation and intramolecular charge transfer of 2‐[2‐(tert‐butyl‐diphenyl‐silanyloxy)‐phenyl]‐4,5‐diphenyl‐1H‐imidazole

Yang

Wang

Chen

et al. 2020

J of Physical Organic Chem

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In view of the tremendous potential for fluorescent chemosensors, more and more people pay attention to design and synthesize high‐efficiency sensors. Given the importance of fluorescence response mechanism, in the present work, the specific sensing mechanism of a novel fluoride anion chemosensor 2‐[2‐(tert‐butyl‐diphenyl‐silanyloxy)‐phenyl]‐4,5‐diphenyl‐1H‐imidazole (abbreviated as TBDI) has been investigated based on density functional theory (DFT) and time‐dependent DFT (TDDFT) methods. Our theoretical electronic spectra (vertical excitation energies and fluorescence emission peaks) reproduced previous experimental results (Sensor Actuat B‐Chem. 2016, 232, 175), which confirms the rationality of our theoretical level adopted in this work. The constructed potential energy curve about fluoride‐triggered desilylation reaction suggests that the low barrier could be responsible for the rapid response to fluoride anion. Analyses about binding energies demonstrate that only fluoride anion could be detected for TBDI chemosensor in dimethyl sulfoxide (DMSO) solvent. In view of the vertical excitation process, the strong intramolecular charge transfer (ICT) process between the S0‐state and S1‐state transition explains the redshift of absorption peak for TBDI sensor with the addition of fluoride anion. This work not only presents a straightforward sensing mechanism of fluoride anion for TBDI sensor but also plays important roles in synthesizing and designing fluorescent chemosensors in future.

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Photodegradation of polybenzimidazole/polyvinyl chloride composites and polybenzimidazole: Density functional theory and experimental study

Jin

Khanal

Zhang

et al. 2020

J of Applied Polymer Sci

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In this study, density functional theory (DFT) and experimental study were conducted to investigate the photodegradation of PVC composites. The results indicate that chain crosslinking, chain scission, dehydrochlorination, and photooxidation are suppressed, while the tensile strength retention of PVC composite reaches a maximum with the incorporation of polybenzimidazole (PBI) and polyacrylic acid modified carbon black. The allyl group can obviously reduce Gibb's free energy (ΔG) of PVC in attack by triplet state oxygen (3 O 2), and photooxidation of PVC is accelerated in the presence of PBI due to the photogeneration of singlet state oxygen (1 O 2). Photodegradation of PBI was also studied by UV-vis spectroscopy and matrix-assisted laser desorption ionization time-of-flight mass spectroscopy, while the possible photodegradation pathways of PBI were proposed. The disappearance of UV-absorption of PBI in PVC matrix after 600 h UVweathering is probably related to the byproducts and molecular properties.

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Structure, spectroscopy, and theory calculations on 1,3-bis((5,6-dimethyl-1H-benzo[d]imidazol-1-yl)methyl)benzene

Cited by 14 publications

References 40 publications

The revelation of ESIPT behavior and fluoride response mechanism for (E)‐2‐(((1H‐benzo[d]imidazol‐2‐yl)‐imino)methyl)‐5‐(dimethylamino)‐phenol

The revelation of ESIPT behavior and fluoride response mechanism for (E)‐2‐(((1H‐benzo[d]imidazol‐2‐yl)‐imino)methyl)‐5‐(dimethylamino)‐phenol

Sensing of fluoride anion based on desilylation and intramolecular charge transfer of 2‐[2‐(tert‐butyl‐diphenyl‐silanyloxy)‐phenyl]‐4,5‐diphenyl‐1H‐imidazole

Photodegradation of polybenzimidazole/polyvinyl chloride composites and polybenzimidazole: Density functional theory and experimental study

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