Synthesis and Structural Analysis of Thiophene-Pyrrole-Based <i>S</i>,<i>N</i>-Heteroacenes

Wetzel, Christoph; Mishra, Amaresh; Mena‐Osteritz, Elena; Liess, Andreas; Stolte, Matthias; Würthner, Frank; Bäuerle, Peter

doi:10.1021/ol403153z

Cited by 67 publications

(76 citation statements)

References 23 publications

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“…In contrast, the onering-shorter derivative SN6 stacks by p-p interactions. [12] Theo ptoelectronic properties of the S,N-heteroacenes were investigated in view of structure-property relationships. Absorption and emission maxima, fluorescence quantum yields,Stokes shifts,optical gaps,oxidation potentials,and the calculated frontier orbital energies are summarized in Table 1.…”

Section: Methodsmentioning

confidence: 99%

“…[11] Thetodate longest S,N-heteroacene,h eterohexacene SN6,w as recently presented by our group and showed interesting optoelectronic properties as well as good charge-carrier mobility. [12] Herein, we report the systematic extension of the S,Nheteroacene series up to as table S,N-heterodecacene SN10. Thes yntheses of novel hexyl-substituted S,N-heteroacenes SN4,t wo SN7 derivatives, SN8, SN9,a nd SN10 in usable amounts is discussed.…”

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confidence: 99%

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Fused Thiophene‐Pyrrole‐Containing Ring Systems up to a Heterodecacene

et al. 2015

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A new class of π-conjugated polycyclic hydrocarbons that promises interesting electronic properties is presented. The synthesis and extension of the S,N-heteroacene series consisting of only five-membered heterocyclic rings up to a very long, stable, and still soluble decacene SN10 is realized by multiple Pd-catalyzed aminations of halogenated thiophene precursors as key reactions. These novel heteroacenes were characterized by optical spectroscopy and electrochemistry providing interesting structure-property relationships. Nearly complete bond-length equalization in the inner part of the conjugated backbone and an unusual herringbone packing in the solid state underline the structural features of these novel systems.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

Fused Thiophene‐Pyrrole‐Containing Ring Systems up to a Heterodecacene

et al. 2015

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“…We recently illustrated these aspects for a series of small organic chromophores used in organic electronics [111]. For three compounds proposed by Bäuerle and collaborators, a dramatic effect of the end groups was noted experimentally [112]. Indeed, adding terminal electroaccepting groups induces strong variations of the position, intensity, and shape of the optical curves.…”

Section: Organic Electronic Chromophoresmentioning

confidence: 99%

Computational Molecular Electronic Spectroscopy with TD-DFT

Jacquemin

Adamo

2015

Topics in Current Chemistry

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In this chapter we present applications of TD-DFT aiming at reproducing and rationalizing the optical signatures of molecules, and, more precisely, the absorption and fluorescence spectra of conjugated compounds belonging to both organic and inorganic families. We particularly focus on the computations going beyond the vertical approximation, i.e., on the calculation of 0-0 energies and vibronic spectra with TD-DFT, and on large applications performed for "real-life" structures (organic and inorganic dyes, optimization of charge-transfer structures, rationalization of excited-state proton transfer, etc.). We present a series of recent applications of TD-DFT methodology for these different aspects. The main conclusions of TD-DFT benchmarks aiming at pinpointing the most suited exchange-correlation functionals are also discussed.

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“…[13] Even higher values have been reported for quadrupolar, p-expanded 1,4-dihydropyrroloA C H T U N G T R E N N U N G [3, 2b]pyrroles, such as 37 (1400 GM). The value of E HOMO for 54 is significantly higher than the values for ladder distyrylbenzenes with silicon and chalcogen bridges, [63] for S,N-heterohexacenes reported by Bäuerle and co-workers, [64] and for dibenzoindoloA C H T U N G T R E N N U N G [3, 2-b]carbazole. The value of E HOMO for 54 is significantly higher than the values for ladder distyrylbenzenes with silicon and chalcogen bridges, [63] for S,N-heterohexacenes reported by Bäuerle and co-workers, [64] and for dibenzoindoloA C H T U N G T R E N N U N G [3, 2-b]carbazole.…”

Section: Physicochemical Propertiesmentioning

confidence: 69%

1,4‐Dihydropyrrolo[3,2‐b]pyrrole and Its π‐Expanded Analogues

Janiga

Gryko

2014

Chemistry An Asian Journal

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Various approaches to the synthesis of 1,4-dihydropyrrolo[3,2-b]pyrroles are summarized. Many two- and three-step reaction sequences have been developed, and have allowed access to a broad variety of structures, including not only the parent 1,4-dihydropyrrolo[3,2-b]pyrroles, but also their π-expanded analogues. The newest approaches are critically compared with older strategies. The reactivity of these compounds is also reviewed, with special emphasis on electrophilic aromatic substitution. The synthesis of indolo[3,2-b]indole derivatives has been the subject of intense investigation. Overall, a few interesting and ingenious approaches toward these ladder-type heteroacenes have been proposed, reaching total yields in the region of 30%. Finally, the optical, electrochemical, and other physicochemical properties are presented in the broader perspective of heteropentalenes. The parent 1,4-dihydro-pyrrolo[3,2-b]pyrroles constitute the most electron-rich, simple, aromatic heterocycles, and their simple derivatives and π-expanded analogues possess strong violet, blue, or green fluorescence both in solution and in the solid state.

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Synthesis and Structural Analysis of Thiophene-Pyrrole-Based S,N-Heteroacenes

Cited by 67 publications

References 23 publications

Fused Thiophene‐Pyrrole‐Containing Ring Systems up to a Heterodecacene

Fused Thiophene‐Pyrrole‐Containing Ring Systems up to a Heterodecacene

Computational Molecular Electronic Spectroscopy with TD-DFT

1,4‐Dihydropyrrolo[3,2‐b]pyrrole and Its π‐Expanded Analogues

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