Effect of End Groups on Mechanochromism and Electroluminescence in Tetraphenylethylene Substituted Phenanthroimidazoles

Jadhav, Thaksen; Choi, Jeong Min; Dhokale, Bhausaheb; Mobin, Shaikh M.; Lee, Jun Yeob; Misra, Rajneesh

doi:10.1021/acs.jpcc.6b06277

Cited by 85 publications

(36 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…TPE is an intriguing material with a unique chemical structure. In previous work, it has demonstrated large NLO coefficients, particularly the first hyperpolarizability or the second-order NLO coefficient, and the four-leaf clover architecture facilitates the design of push-pull chromophores that allows electron charge transfer across the π conjugation of the TPE molecule [170][171][172][173][174][175][176][177][178][179]. It has previously been used successfully as an imaging agent [155,155,180], and, in contrast to many fluorophores, it is well-known for exhibiting aggregation-induced-emission (AIE) [171,181] in which the emission intensity increases as the molecules aggregate.…”

Section: Organic Materialsmentioning

confidence: 99%

Nonlinear nanophotonic devices in the ultraviolet to visible wavelength range

Chen

et al. 2020

Nanophotonics

View full text Add to dashboard Cite

AbstractAlthough the first lasers invented operated in the visible, the first on-chip devices were optimized for near-infrared (IR) performance driven by demand in telecommunications. However, as the applications of integrated photonics has broadened, the wavelength demand has as well, and we are now returning to the visible (Vis) and pushing into the ultraviolet (UV). This shift has required innovations in device design and in materials as well as leveraging nonlinear behavior to reach these wavelengths. This review discusses the key nonlinear phenomena that can be used as well as presents several emerging material systems and devices that have reached the UV–Vis wavelength range.

show abstract

Section: Organic Materialsmentioning

confidence: 99%

Nonlinear nanophotonic devices in the ultraviolet to visible wavelength range

Chen

et al. 2020

Nanophotonics

View full text Add to dashboard Cite

show abstract

“…Although several attempts have been made to develop TPE‐based AIE emitters so far, their performances lack in terms of low device efficiency and high efficiency roll‐off . In addition, a lot imidazole‐based emitters (some also containing TPE units) were also synthesized to date, but could not meet the required performance . In this work, we have adopted a strategy to combine highly emissive moieties in a twisted conformation to achieve efficient blue luminogens.…”

Section: Methodsmentioning

confidence: 91%

“…All the devices exhibited reasonably low driven voltage. The device performance of 3TPEI is better than several materials (including TPE‐containing materials) reported for non‐doped sky blue OLED devices . The data of electroluminescence performance of the devices is summarized in Table .…”

Section: Methodsmentioning

confidence: 99%

“…[27,33,34,[41][42][43] In addition, al ot imidazole-based emitters (some also containing TPE units) were also synthesized to date, but could not meet the required performance. [44,45] In this work, we have adopted as trategy to combine highly emissive moieties in at wisted conformation to achieve efficient blue luminogens. In this way, we can solve different issues such as controlling the extension of conjugation and removing stacking interactions that usually lead to weak and red-shifted emission in luminogens.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Non‐Doped Sky‐Blue OLEDs Based on Simple Structured AIE Emitters with High Efficiencies at Low Driven Voltages

Islam

Zhang

Peng

et al. 2017

Chemistry An Asian Journal

View full text Add to dashboard Cite

Blue organic light-emitting diodes (OLEDs) are necessary for flat-panel display technologies and lighting applications. To make more energy-saving, low-cost and long-lasting OLEDs, efficient materials as well as simple structured devices are in high demand. However, a very limited number of blue OLEDs achieving high stability and color purity have been reported. Herein, three new sky-blue emitters, 1,4,5-triphenyl-2-(4-(1,2,2-triphenylvinyl)phenyl)-1H-imidazole (TPEI), 1-(4-methoxyphenyl)-4,5-diphenyl-2-(4-(1,2,2-triphenylvinyl)phenyl)-1H-imidazole (TPEMeOPhI) and 1-phenyl-2,4,5-tris(4-(1,2,2-triphenylvinyl)phenyl)-1H-imidazole (3TPEI), with a combination of imidazole and tetraphenylethene groups, have been developed. High photoluminescence quantum yields are obtained for these materials. All derivatives have demonstrated aggregation-induced emission (AIE) behavior, excellent thermal stability with high decomposition and glass transition temperatures. Non-doped sky-blue OLEDs with simple structure have been fabricated employing these materials as emitters and realized high efficiencies of 2.41 % (4.92 cd A , 2.70 lm W ), 2.16 (4.33 cd A , 2.59 lm W ) and 3.13 % (6.97 cd A , 4.74 lm W ) for TPEI, TPEMeOPhI and 3TPEI, with small efficiency roll-off. These are among excellent results for molecules constructed from the combination of imidazole and TPE reported so far. The high performance of a 3TPEI-based device shows the promising potential of the combination of imidazole and AIEgen for synthesizing efficient electroluminescent materials for OLED devices.

show abstract

“…Fluorescent materials that respond to external stimuli are of great interest, both from a fundamental materials science perspective and with respect to practical applications in sensors, security papers, optoelectronic switches, and information‐storage devices . Especially methods to control the self‐assembly structures of such materials in the solid state or in solution have attracted much attention, due to the potential utility in switchable dual‐emission materials .…”

Section: Figurementioning

confidence: 99%

Self‐Assembly and Fluorescence Properties of [60]Fullerene‐Pentacene Monoadducts

et al. 2017

View full text Add to dashboard Cite

The highly soluble [60]fullerene-pentacene monoadducts 2 a and 2 b were synthesized by a Diels-Alder reaction between [60]fullerene and pentacene derivatives. The single-crystal X-ray diffraction analysis of 2 a revealed an attractive intermolecular interaction between [60]fullerene moiety of one molecule and the pentacene arms of an adjacent molecule, resulting in the formation of head-to-tail dimers in solution. This self-association behavior of 2 a and 2 b was also observed by 1 H NMR and fluorescence spectroscopy in chloroform. Both the excitation and emission wavelengths can be modulated via the concentration of 2 a and 2 b.Fluorescent materials that respond to external stimuli [1][2][3][4] are of great interest, both from a fundamental materials science perspective and with respect to practical applications in sensors, [5,6] security papers, [7,8] optoelectronic switches, [9,10] and information-storage devices. [11,12] Especially methods to control the self-assembly structures of such materials in the solid state or in solution have attracted much attention, due to the potential utility in switchable dual-emission materials. [13][14][15][16][17][18][19][20][21][22][23][24][25][26] However, examples for molecules that are capable of switching the wavelength of not only the emission but also the excitation by changing their self-assembled structures remain scarce. [27,28] Fullerene-pentacene monoadducts represent in this context highly promising prospectives, as they exhibit switchable dual emission and dual excitation on account of the presence of two fluorophores (fullerene and naphthalene moieties) and their nested crystal packing, i. e., each fullerene moiety nests within the pentacene arms of an adjacent monoadduct via p-p interactions. [29][30][31][32] However, studies on the self-association and fluorescence behavior of fullerene-pentacene monoadducts in solution have not yet been reported, most likely due to a lack of soluble derivatives. We were therefore interested in preparing highly soluble fullerene-pentacene monoadducts. Herein, we describe the self-assembly and fluorescence properties of [60]fullerene-pentacene monoadducts in solution.Highly soluble [60]fullerene-pentacene monoadducts 2 a and 2 b were synthesized by Diels-Alder reactions between [60] fullerene and the previously reported pentacene derivatives 1 a and 1 b, [33] respectively (Scheme 1). A solution of 1 a and [60] fullerene in o-dichlorobenzene was stirred for 20 h at 45 8C under an atmosphere of argon in the dark. After purification by column chromatography on silica gel (eluent: CHCl 3 ) and GPLC (CHCl 3 ), brown crystals of 2 a were obtained in 89 % yield. A similar reaction using 1 b instead of 1 a afforded 2 b in 75 % yield. As expected, 2 a and 2 b are highly soluble in various organic solvents including toluene, benzene, benzonitrile, THF, chloroform, and dichloromethane. Moreover, 2 a and 2 b are stable in the dark and can be kept for several months at room temperature, i. e., retro-Diels-Alder reactions of 2 a and 2 b ...

show abstract

Effect of End Groups on Mechanochromism and Electroluminescence in Tetraphenylethylene Substituted Phenanthroimidazoles

Cited by 85 publications

References 34 publications

Nonlinear nanophotonic devices in the ultraviolet to visible wavelength range

Nonlinear nanophotonic devices in the ultraviolet to visible wavelength range

Non‐Doped Sky‐Blue OLEDs Based on Simple Structured AIE Emitters with High Efficiencies at Low Driven Voltages

Self‐Assembly and Fluorescence Properties of [60]Fullerene‐Pentacene Monoadducts

Contact Info

Product

Resources

About