Synthesis and characterization of propeller-shaped mono- to hexacationic quinolinium-substituted benzenes

Batsyts, Sviatoslav; Hübner, Eike G.; Namyslo, Jan C.; Gjikaj, Mimoza; Schmidt, Andreas

doi:10.1039/c9ob00357f

Cited by 11 publications

(13 citation statements)

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“…First, 1,4‐diethynylbenzene 8 was synthesized in two steps from 1,4‐dibromobenzene 6 and 2‐methyl‐butyn‐2‐ol (MEBYNOL) via 7 according to modified literature‐known procedures (Scheme ). The non‐symmetric ethynyl quinolines 10a,b were finally prepared in two consecutive Sonogashira reactions …”

Section: Resultssupporting

confidence: 91%

“…Subsequently, 1,4‐diethynylbenzene 8 was treated with an excess of halogenated quinolines under Sonogashira conditions to give the symmetric ethynyl quinolines 10c–e , (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…The non-symmetric ethynyl quinolines 10a,b were finally prepared in two consecutive Sonogashira reactions. [19] Subsequently, 1,4-diethynylbenzene 8 was treated with an excess of halogenated quinolines under Sonogashira conditions to give the symmetric ethynyl quinolines 10c-e [18,19] (Scheme 4).…”

Section: Resultsmentioning

confidence: 99%

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The Interconnection of Two Positive Charges by Conjugation and Cross‐Conjugation in Bis‐Quinolinium Ethynyls

et al. 2019

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1,4‐Diethynylbenzene was used as conjugated all‐carbon and rigid spacer between the 2‐, 3‐ and 4‐positions of two 1‐methylquinolinium rings. Thus, for a systematic study, a series of dicationic salts with 2,2‐, 3,3‐, 4,4‐, 3,2‐, and 3,4‐interconnections of the two positive charges was prepared, in which all even‐numbered substitution patterns are conjugated, and all odd‐numbered substitution patterns are cross‐conjugated. As a consequence, conjugated/conjugated, cross‐conjugated/cross‐conjugated, and conjugated/cross‐conjugated dications have been prepared. The different combinations result in considerably different charge distributions of the positive charges within the π‐electron systems according to the rules of resonance which translate into different DFT‐calculated frontier orbital profiles and spectroscopic properties such as 13C NMR chemical shifts, IR and Raman absorptions, and the measured as well as calculated UV/Vis spectra.

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Section: Resultssupporting

confidence: 91%

“…Subsequently, 1,4‐diethynylbenzene 8 was treated with an excess of halogenated quinolines under Sonogashira conditions to give the symmetric ethynyl quinolines 10c–e , (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

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The Interconnection of Two Positive Charges by Conjugation and Cross‐Conjugation in Bis‐Quinolinium Ethynyls

et al. 2019

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“…Neutral precursors were obtained via cyclotrimerization of appropriately substituted acetylenes (for instance hexa-substituted one) or using DA cycloaddition among adequately substituted acetylenes and tetraphenylacetylene. The syntheses involving DA cycloaddition are shown in Scheme 144 [ 198 ].…”

Section: Cyclopentadienones For the Multisubstituted Benzene Ring And Naphthalene System Formationmentioning

confidence: 99%

Diels–Alder Cycloaddition with CO, CO2, SO2, or N2 Extrusion: A Powerful Tool for Material Chemistry

et al. 2021

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Phenyl, naphthyl, polyarylphenyl, coronene, and other aromatic and polyaromatic moieties primarily influence the final materials’ properties. One of the synthetic tools used to implement (hetero)aromatic moieties into final structures is Diels–Alder cycloaddition (DAC), typically combined with Scholl dehydrocondensation. Substituted 2-pyranones, 1,1-dioxothiophenes, and, especially, 1,3-cyclopentadienones are valuable substrates for [4 + 2] cycloaddition, leading to multisubstituted derivatives of benzene, naphthalene, and other aromatics. Cycloadditions of dienes can be carried out with extrusion of carbon dioxide, carbon oxide, or sulphur dioxide. When pyranones, dioxothiophenes, or cyclopentadienones and DA cycloaddition are aided with acetylenes including masked ones, conjugated or isolated diynes, or polyynes and arynes, aromatic systems are obtained. This review covers the development and the current state of knowledge regarding thermal DA cycloaddition of dienes mentioned above and dienophiles leading to (hetero)aromatics via CO, CO2, or SO2 extrusion. Particular attention was paid to the role that introduced aromatic moieties play in designing molecular structures with expected properties. Undoubtedly, the DAC variants described in this review, combined with other modern synthetic tools, constitute a convenient and efficient way of obtaining functionalized nanomaterials, continually showing the potential to impact materials sciences and new technologies in the nearest future.

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“…The very sterically hindered structure of both substituents could well‐split up the molecules from being closely interacted. [ 23 ] Simultaneously, the different molecular orientations of naphthalene and 1,1′‐biphenyl parts with a weak electron‐donating feature could offer a fine tune in molecular packing of the molecules and lessen bathochromic shift by weakening intramolecular CT and limiting the π‐conjugation of the structure to retain deep‐blue emission. Indeed, these newly synthesized anthracene‐based emitters possessed TTA features with deep‐blue emission in solution.…”

Section: Introductionmentioning

confidence: 99%

A Dimeric π‐Stacking of Anthracene Inducing Efficiency Enhancement in Solid‐State Fluorescence and Non‐Doped Deep‐Blue Triplet–Triplet Annihilation Organic Light‐Emitting Diodes

Nalaoh

Sungworawongpana

Chasing

et al. 2021

Advanced Optical Materials

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Triplet–triplet annihilation (TTA) mechanism utilizing the conversion of low triplet energy excitons to generate singlet excitons has been successfully employed in realizing highly efficient fluorescent organic light‐emitting diodes (OLEDs). Herein, new anthracene‐based TTA molecules (TPNACN and TPBACN) are developed as deep‐blue emitters for high‐efficiency non‐doped TTA‐OLEDs. Their structural, physical, and photophysical properties are experimentally and theoretically investigated. These compounds in solid‐state exhibit different photophysical properties due to a discrepancy in the molecular packing. Particularly, in the crystal of TPNACN, anthracene moieties are arranged with dimeric π–π stacking, and the material shows a strong excimer emission in the deep‐blue region with ΦPL close to the ideal theoretical value. The non‐doped TTA‐OLED based on TPNACN attains a high maximum external quantum efficiency of 7.89% (6.63 cd A−1) with a low turn‐on voltage of 2.6 V, and displays deep‐blue emission with CIE coordinates of (0.146, 0.101). These results prove that a separated dimeric π‐stacked molecular alignment of anthracene enhances not only the fluorescence efficiency in the solid state but also the ratio of singlet exciton harvested by the TTA process in the device, bringing about excellent device electroluminescent properties. This can be a new tactic to designing new emissive materials for efficient OLED devices.

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Synthesis and characterization of propeller-shaped mono- to hexacationic quinolinium-substituted benzenes

Abstract: In propeller-shaped molecules a central benzene core is substituted by up to six N-methylquinolinium rings.

Cited by 11 publications

References 77 publications

The Interconnection of Two Positive Charges by Conjugation and Cross‐Conjugation in Bis‐Quinolinium Ethynyls

The Interconnection of Two Positive Charges by Conjugation and Cross‐Conjugation in Bis‐Quinolinium Ethynyls

Diels–Alder Cycloaddition with CO, CO2, SO2, or N2 Extrusion: A Powerful Tool for Material Chemistry

A Dimeric π‐Stacking of Anthracene Inducing Efficiency Enhancement in Solid‐State Fluorescence and Non‐Doped Deep‐Blue Triplet–Triplet Annihilation Organic Light‐Emitting Diodes

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