Efficient synthesis of 5-oxatruxene and the unusual influence of oxygen heteroatom on its physico-chemical properties

A thorough investigation has enabled the optimization of the synthesis of 1,4-dihydro-pyrrolo[3,2- b ]pyrroles. Although salts of such metals as vanadium, niobium, cerium, and manganese were found to facilitate the formation of 1,4-dihydro-pyrrolo[3,2- b ]pyrroles from amines, aldehydes, and diacetyl, we confirmed that iron salts are the most efficient catalysts. The conditions identified (first step: toluene/AcOH = 1:1, 1 h, 50 °C; second step: toluene/AcOH = 1:1, Fe(ClO 4 ) 3 ·H 2 O, 16 h, 50 °C) resulted in the formation of tetraarylpyrrolo[3,2- b ]pyrroles in a 6–69% yield. For the first time, very electron-rich substituents (4-Me 2 NC 6 H 4 , 3-(OH)C 6 H 4 , pyrrol-2-yl) originating from aldehydes and sterically hindered substituents (2-ClC 6 H 4 , 2-BrC 6 H 4 , 2-CNC 6 H 4 , 2-(CO 2 Me)C 6 H 4 , 2-(TMS-C≡C)C 6 H 4 ) present on anilines can be appended to the pyrrolo[3,2- b ]pyrrole core. It is now also possible to prepare 1,4-dihydropyrrolo[3,2- b ]pyrroles bearing an ordered arrangement of N -substituents and C -substituents ranging from coumarin, quinoline, phthalimide to truxene. These advances in scope enable independent regulations of many desired photophysical properties, including the Stokes shift value and emission color ranging from violet-blue through deep blue, green, yellow to red. Simultaneously, the optimized conditions have finally allowed the synthesis of these extremely promising heterocycles in amounts of more than 10 g per run without a concomitant decrease in yield or product contamination. Empowered with better functional group compatibility, novel derivatization strategies were developed.

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“…One of the factors responsible for the observed excellent emissive properties could be symmetry-breaking within the truxene core. 36 …”

Section: Resultsmentioning

confidence: 99%

Method for the Large-Scale Synthesis of Multifunctional 1,4-Dihydro-pyrrolo[3,2-b]pyrroles

et al. 2020

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“…Compound CCC was synthesized according to known literature procedures, 56 and OCC, SCC, (OS)CC, and (O2S)CC were obtained using synthetic routes published by our group. 57,58 Herein we describe an alternative synthetic pathway, improving on the initial approach, to access azatruxene derivative NCC, which we very recently reported for the rst time. 58 2-(Indan-1ylidene)indan-1-one 1, which is a product of the acid promoted, silicon mediated aldol cross-condensation of indan-1-one, turned out to be a valuable building block in the synthesis of OCC and SCC.…”

Section: Synthetic Proceduresmentioning

confidence: 99%

“…6. 57 The presence of six ethyl groups in the CCC molecule, oriented above and below the plane of the aromatic system, effectively limits intermolecular interactions between the p-electron systems. For this reason, there are no shis in the absorption bands when passing from a solution to a solid state.…”

Section: Table 1 Spectroscopic Data Of Ethylated Truxene and 5-heteromentioning

confidence: 99%

Influence of the heteroatom introduction on the physicochemical properties of 5-heterotruxenes containing nitrogen, oxygen and sulfur atom

2020

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“…This has been followed by introducing other heteroatoms to truxene core like oxygen, leading to oxatruxene, a molecule with enhanced fluorescence quantum yield in comparison to its allcarbon counterpart by factor of 4. [70] Bright blue light-emitting materials for application in displays are of high demand but they need to meet certain criteria of color purity: Commission Internationale de L'Eclairage coordinates (CIE x, y) of (0.14, 0.08) are required by the National Television System Committee (NTSC) while High-Definition Television (HDTV) ITU-R BT.709 requires a deeper blue emission with CIE x, y of (0.15, 0.06). Typically, in the literature the deep blue emission is defined as having a CIE coordinates y < 0.15 and x + y < 0.30.…”

Section: Introductionmentioning

confidence: 99%

Monothiatruxene‐Based, Solution‐Processed Green, Sky‐Blue, and Deep‐Blue Organic Light‐Emitting Diodes with Efficiencies Beyond 5% Limit

Maciejczyk

Zhang

Hedley

et al. 2018

Adv Funct Materials

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The development of blue materials with good efficiency, even at high brightness, with excellent color purity, simple processing and high thermal stability assuring adequate device lifetime is an important remaining challenge for organic light-emitting didoes (OLEDs) in displays and lightning applications. Furthermore, these various features are typically mutually exclusive in practice. Herein, four novel green and blue light emitting materials based on a monothiatruxene core are reported together with their photophysical and thermal properties, and performance in solution-processed OLEDs. The materials showed excellent thermal properties with high glass transition temperatures ranging from 171 °C to 336 °C and decomposition temperatures from 352 °C to 442 °C. High external quantum efficiency of 3.7 % for a deep blue emitter with C.I.E. color co-ordinates (0.16, 0.09) and 7% for green

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Efficient synthesis of 5-oxatruxene and the unusual influence of oxygen heteroatom on its physico-chemical properties

Abstract: 5-Oxatruxene presents new quality among the truxenes. It is a promising compound for the new class of optoelectronic materials.

Cited by 13 publications

References 56 publications

Method for the Large-Scale Synthesis of Multifunctional 1,4-Dihydro-pyrrolo[3,2-b]pyrroles

Method for the Large-Scale Synthesis of Multifunctional 1,4-Dihydro-pyrrolo[3,2-b]pyrroles

Influence of the heteroatom introduction on the physicochemical properties of 5-heterotruxenes containing nitrogen, oxygen and sulfur atom

Monothiatruxene‐Based, Solution‐Processed Green, Sky‐Blue, and Deep‐Blue Organic Light‐Emitting Diodes with Efficiencies Beyond 5% Limit

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