Hydroxyphenyl-benzothiazole based full color organic emitting materials generated by facile molecular modification

Yao, Dandan; Zhao, Shanshan; Guo, Jian‐Hua; Zhang, Zuolun; Zhang, Hongyu; Liu, Yu; Wang, Yue

doi:10.1039/c1jm00009h

Cited by 121 publications

(73 citation statements)

References 15 publications

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“…The amino substituted HBT compounds with ESIPT processes show novel fluorescence characteristics (4‐substituted and 5‐substituted compounds). Yao and coworkers designed and synthesized the (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol (HBT‐Cz), which exhibits the contrary shifts in solid photoluminescence (PL) and electroluminescence (EL) spectra upon the variation of substituted groups on amino from dimethylamino to diphenylamino and to carbazole. Very recently, Mai and coworkers show a novel in‐depth investigation of HBT‐Cz, which reveals that HBT‐Cz is a solution‐processable organic small molecule dyes.…”

Section: Introductionmentioning

confidence: 99%

A detailed theoretical simulation about the excited state dynamical process for the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol molecule

Zhang

Cheng

et al. 2019

J of Physical Organic Chem

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Given that molecular excited state dynamical process plays important roles in designing and developing novel applications in recent years. In this work, based on density functional theory (DFT) and time‐dependent density functional theory (TDDFT) methods, we theoretically explored the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol (HBT‐Cz) system about its excited state behaviors. Via simulating the electrostatic potential surface (EPS) of HBT‐Cz structure, we confirm the formation of intramolecular hydrogen bond O2—H3···N4 in the S0 state. Our theoretical dominating bond lengths, bond angles, and the infrared (IR) vibrational spectra involved in hydrogen bond demonstrate that O2—H3···N4 should be strengthened in the S1 state. Upon the photoexcitation, we find the charge transfer characteristics around hydrogen bonding moieties play important roles in facilitating excited state intramolecular proton transfer (ESIPT) process. Via constructing potential energy curves, we confirm the ESIPT reaction that further explains previous experimental phenomenon. Moreover, we also search the S1‐state transition state (TS) structure along with ESIPT path, based on which we simulate the intrinsic reaction coordinate (IRC) path. Combing with the atom‐centered density matrix propagation (ADMP) molecular dynamics simulation, we further confirm the ESIPT mechanism presented in this work. We sincerely hope that our theoretical work could guide novel applications based on HBT‐Cz system in future.

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Section: Introductionmentioning

confidence: 99%

A detailed theoretical simulation about the excited state dynamical process for the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol molecule

Zhang

Cheng

et al. 2019

J of Physical Organic Chem

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“…51,52 As clearly demonstrated in Figures 6 and S1, all photoluminescence maxima of X-oHBI (where X = NO 2 and EC, i.e., electron withdrawing groups (EWGs)) are hypsochromically shifted relative to X-oHBI (where X = MeO, Me, OH, and t Bu, i.e., electron donating groups (EDGs)). However, the observed behavior in the case of X-oHBI (where X = F, Cl, and Br, i.e., halogens) is close to that of X-oHBI (X = EDG).…”

Section: Inorganic Chemistrymentioning

confidence: 92%

Photophysics, Dynamics, and Energy Transfer in Rigid Mimics of GFP-based Systems

et al. 2016

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Engineering of novel systems capable of efficient energy capture and transfer in a predesigned pathway could potentially boost applications varying from organic photovoltaics to catalytic platforms and have implications for energy sustainability and green chemistry. While light-harvesting properties of different materials have been studied for decades, recently, there has been great progress in the understanding and modeling of short- and long-range energy transfer processes through utilization of metal-organic frameworks (MOFs). In this Forum Article, the recent advances in efficient multiple-chromophore coupling in well-defined metal-organic materials through mimicking a protein system possessing near 100% energy transfer are discussed. Utilization of a MOF as an efficient replica of a protein β-barrel to maintain chromophore emission was also demonstrated. Furthermore, we established a novel dependence of a photophysical response on an electronic configuration for chromophores with the benzylidene imidazolinone core. For that, we prepared 16 chromophores, in which the benzylidene imidazolinone core was modified with electron-donating and electron-withdrawing substituents. To establish the structure-dependent photophysical properties of the prepared chromophores, 11 novel molecular structures were determined by single-crystal X-ray diffraction. These findings allow one to predict the chromophore emission profile inside a rigid framework as a function of the substituent, a key parameter for achieving the spectral overlap necessary to study and increase resonance energy transfer efficiency in MOF-based materials.

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“…Similarly emission band at 490 nm was observed for 6b, along the major emission band at 515 nm. The multi emission of organic fluorophores is in particular interesting for applications such as white light electroluminescence or luminescent bio imaging [7,[16][17][18][19][20][21]. The photophysical properties of the compounds are summarized in Table 1 and Figs.…”

Section: Optical Propertiesmentioning

confidence: 99%

“…The molecules exhibiting ESIPT have been exploited as model systems for the study of the proton transfer reaction dynamics [3,4]. The ESIPT reaction, a fast enol-to-keto or (amine-to-imine) prototropy occurring in the excited states of intramolecularly hydrogen-bonded molecules, has been extensively investigated because of its fundamental interest in photophysical properties and potential applications in luminescent materials [5], photo patterning [6], chemosensors [7], proton transfer laser [8], photo stabilizers [9,10], molecular logic gates [11], molecular probes [12], metal ion sensors [13,14], radiation hard-scintillator counters [15], and organic light emitting devices (OLEDs) [16,17], The ESIPT compounds have also drawn much attention due to their potential applications in optical devices [18,19] that may take advantage of the salient properties of the ESIPT compounds such as the ultra-fast reaction rate and extremely large fluorescence Stokes shift [20] compared to the normal fluorophores such as fluorescein, rhodamine or boron dipyrromethene (BODIPY), coumarin [21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Novel 6-(1H-benzo[d]imidazol-2-yl) benzo[a]phenazin-5-ol Derivatives with Dual Emission and Large Stokes Shift Synthesis, Photophysical Properties and Computational Studies

Choudhary

Sekar

2015

J Fluoresc

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Novel phenazine containing dyes were obtained by the condensation of 5-hydroxybenzo[a]phenazine-6-carbaldehyde and 5-chloro-benzo[a]phenazine-6-carbaldehyde with 1,2-diaminobenzene. The dyes were characterized by FT-IR, 1H NMR, elemental analysis and mass spectra. The UV-vis absorption and fluorescence emission spectra of the dyes were studied in solvents of differing polarity; the dyes exhibited excited state intra molecular proton transfer. The structural changes due to excited state intramolecular proton transfer (ESIPT) phenomenon in terms of bond angle, bond distances and geometry were investigated with the help of DFT computations. The computed absorption and emission were in agreement with the experimental absorption and emission.

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Hydroxyphenyl-benzothiazole based full color organic emitting materials generated by facile molecular modification

Abstract: Two sets of hydroxyphenyl-benzothiazole based compounds, which exhibited emission colors across the entire visible spectrum for both photoluminescence and electroluminescence, have been designed and synthesized.

Cited by 121 publications

References 15 publications

A detailed theoretical simulation about the excited state dynamical process for the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol molecule

A detailed theoretical simulation about the excited state dynamical process for the novel (benzo[d]thiazol‐2‐yl)‐5‐(9H‐carbazol‐9‐yl)phenol molecule

Photophysics, Dynamics, and Energy Transfer in Rigid Mimics of GFP-based Systems

Novel 6-(1H-benzo[d]imidazol-2-yl) benzo[a]phenazin-5-ol Derivatives with Dual Emission and Large Stokes Shift Synthesis, Photophysical Properties and Computational Studies

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