Liquid Crystalline Coronene Derivatives with Extraordinary Fluorescence Properties

Rohr, U.; Schlichting, P.; Böhm, A.; Groß, Markus; Meerholz, Klaus; Bräuchle, Christoph; Müllen, Kläus

doi:10.1002/(sici)1521-3773(19980605)37:10<1434::aid-anie1434>3.0.co;2-p

Cited by 193 publications

(20 citation statements)

References 5 publications

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“…These exotherms are likely a result of a possible cyclization reaction occurring between the triple bonds and the carbonyl groups in NDI 34 or aromatic rings in PTCDI. 35,36 Our attempt to characterize the materials after the DSC experiment was unsuccessful as the materials after thermal treatment were intractable.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Understanding the Electronic Properties of Acceptor–Acceptor′–Acceptor Triads

et al. 2019

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In order to develop new organic materials for optoelectronic applications, a fundamental understanding of the electronic properties of specific chromophore combinations must be realized. To that end, we report “model” acceptor (A)–acceptor′ (A′)–acceptor (A) triads in which the pendants (A′) we selected are well-known components of organic optoelectronic applications. Our pendants are sandwiched between two dialkoxyphenazine (A) through an alkyne bond. The A′ was systematically increased in electron-deficiency from benzothiadiazole ( BTD-P ) to naphthalene diimide with octyl ( NDI-O-P ) or ethylhexyl groups ( NDI-EH-P ) to perylene diimide with ethylhexyl ( PTCDI-EH-P ) to assess changes in the electronic properties of the resultant molecules. Characterizations were performed using both experimental and theoretical methods. From optical and cyclic voltammetry, we found that the electron deficiency of each pendant was directly correlated to the energy level of the lowest unoccupied molecular orbital ( E LUMO ). When examining the simple molecular orbital diagrams produced at the B3LYP/6-31G* level of theory, the LUMOs were, as expected, primarily localized on the more electron-deficient pendants. In terms of the energy level of the highest occupied molecular orbital ( E HOMO ), the numerical values obtained experimentally also correlated with values obtained computationally. Attempting to construct a simplified model that would explain these correlated values was not as readily apparent, given the disparate physical characteristics of these compounds. For example, BTD-P and NDI-O-P/NDI-EH-P achieved planarity when computationally optimized, but PTCDI-EH-P adapted a “buckled” geometry on the central PTCDI, consequently forcing the attached phenazines out-of-plane. The title compounds showed solvent polarity-dependent fluorescence, which is indicative of intramolecular charge transfer. In conjunction with our theoretical study, the current system can be viewed as an extension of donor–acceptor–donor systems. Thermal properties characterized by differential scanning calorimetry revealed that reversible phase transitions were only observed for BTD-P . In addition, BTD-P was found to be an efficient gelator in 1,1,1-trichloroethane and toluene. The other compounds in this study did not form gels in any of the solvents tested, which may have been a result of the alkyl groups on the pendants hampering the fibrillation process.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Understanding the Electronic Properties of Acceptor–Acceptor′–Acceptor Triads

et al. 2019

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“…Bulk-phase PIs have been widely used in various optoelectronics devices [29][30][31], including thin-film transistors [32,33], photovoltaics [34,35], liquid crystals [36,37] and chemiresistive sensors [38], etc. Performance of optical chemosensors (as well the devices fabricated therefrom) depends primarily on the physicochemical and optical properties of the sensing materials, here specifically the fluorophores or chromophores, which in turn are tightly correlated with the molecular design and structure engineering [28,29,39].…”

Section: Physicochemical and Optical Properties Of Pismentioning

confidence: 99%

Perylene Imide-Based Optical Chemosensors for Vapor Detection

et al. 2020

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Perylene imide (PI) molecules and materials have been extensively studied for optical chemical sensors, particularly those based on fluorescence and colorimetric mode, taking advantage of the unique features of PIs such as structure tunability, good thermal, optical and chemical stability, strong electron affinity, strong visible light absorption and high fluorescence quantum yield. PI-based optical chemosensors have now found broad applications in gas phase detection of chemicals, including explosives, biomarkers of some food and diseases (such as organic amines (alkylamines and aromatic amines)), benzene homologs, organic peroxides, phenols and nitroaromatics, etc. In this review, the recent research on PI-based fluorometric and colorimetric sensors, as well as array technology incorporating multiple sensors, is reviewed along with the discussion of potential applications in environment, health and public safety areas. Specifically, we discuss the molecular design and aggregate architecture of PIs in correlation with the corresponding sensor performances (including sensitivity, selectivity, response time, recovery time, reversibility, etc.). We also provide a perspective summary highlighting the great potential for future development of PIs optical chemosensors, especially in the sensor array format that will largely enhance the detection specificity in complexed environments.

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“…60 Finally base induced double cyclisation of 3 gave the desired bisindoloanthracene 4. 61,62 In the realm of organic electronics, base catalysed isomerisation of alkynylated oligomers to polyaromatic semiconductors has been used for the synthesis of coronenes 63,64,65,66 and thienoacenes of various number of rings and sulfur atoms. 67,68,69,70 Here, we demonstrate that this strategy is also suitable for the synthesis of bis-[(1,2)(5,6)]indoloanthracene (4) a new π-extended nitrogen based heterocycle.…”

Section: Computational Detailsmentioning

confidence: 99%

Highly Luminous Sky-Blue Organic Light-Emitting Diodes Based on the Bis[(1,2)(5,6)]indoloanthracene Emissive Layer

et al. 2016

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An in-depth analysis of the electro-optical and light emissive properties was carried out with a new fused heteroacene, the bis [(1,2)(5,6)] indoloanthracene. The compound was synthesized in a straightforward bidirectional manner from 1,4-dibromo-2,5-diodobenzene utilizing a reaction cascade of isomerisation and cyclisation sequences. Bis-[(1,2)(5,6)] indoloanthracene exhibits bright luminescence with high quantum yield in solution as well as in the solid state. By using this novel semiconductor as active layer, an efficient OLED has been fabricated for which its emission pattern resembles at least two emitters in a single emissive region originated from the same molecule. One has its origin from the single molecule and is similar to the luminescence spectra in solution, whereas the other functions through the formation of aggregates being similar with the emission pattern found with crystals of bis-[(1,2)(5,6)]indoloanthracene. As a result bright sky-blue OLEDs with very high luminance exceeding 10000 cd/m 2 were obtained. Such color pattern and performance has not previously been observed with low molecular weight, electron-rich fused polycyclic aromatic compounds and indicate a promising new class of materials for development.

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Liquid Crystalline Coronene Derivatives with Extraordinary Fluorescence Properties

Cited by 193 publications

References 5 publications

Understanding the Electronic Properties of Acceptor–Acceptor′–Acceptor Triads

Understanding the Electronic Properties of Acceptor–Acceptor′–Acceptor Triads

Perylene Imide-Based Optical Chemosensors for Vapor Detection

Highly Luminous Sky-Blue Organic Light-Emitting Diodes Based on the Bis[(1,2)(5,6)]indoloanthracene Emissive Layer

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