SFB 1249: N-Heteropolyzyklen als Funktionsmaterialien

The SFB 1249 is an interdisciplinary Collaborative Research Centre at Heidelberg University with project partners at the Karlsruhe Institute of Technology (KIT), MPI for Solid State Research in Stuttgart, University of Kassel and the Heidelberg Institute for Theoretical Studies (HITS). It is funded by the German Research Foundation (DFG).

The aim of this SFB is the development of novel organic functional materials with specifically tailored electronic properties and their application as photoactive components and organic semiconductors. We focus on the molecular class of N-heteropolycycles, which provide a wide range of tunable structures. Research areas include Synthesis (A), Theory and Structure (B), and Material and Function (C).

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11 to 20 of 51 Results

Zipping up Tetraazaperylene: Synthesis of Tetraazacoronenes via Double Coupling in the Bay Positions [data] Feb 20, 2024 - Gade Group Eichelmann, Robert; Rippel, Daniel; Ballmann, Joachim; Gade, Lutz H., 2024, "Zipping up Tetraazaperylene: Synthesis of Tetraazacoronenes via Double Coupling in the Bay Positions [data]", https://doi.org/10.11588/data/HIERR9, heiDATA, V1 Substituted tetraazacoronene fluorophores have been obtained selectively by double Suzuki–Miyaura cross coupling of symmetrically substituted 1,2-bis(pinacolatoboryl)alkenes with a bay-substituted octaazaperopyrenedioxide (OAPPDO). Subsequent Scholl reaction of the dimethoxypheny...
Chiral Bay-Alkynylated Tetraazaperylenes: Photophysics and Chiroptical Properties Feb 20, 2024 - Gade Group Eichelmann, Robert; Jeudy, Pierre; Schneider, Lars; Zerhoch, Jonathan; Mayer, Paula R.; Ballmann, Joachim; Deschler, Felix; Gade, Lutz H., 2024, "Chiral Bay-Alkynylated Tetraazaperylenes: Photophysics and Chiroptical Properties", https://doi.org/10.11588/data/PGSVXO, heiDATA, V1 Fully bay-alkynylated octaazaperopyrene dioxide (OAPPDO) derivatives were accessible through Stille cross coupling reaction of the corresponding bay-chlorinated derivatives. This steric congestion of the bay area led to helically chiral fluorophores, and chiral resolution of two...
Tetraazacoronenes and Their Dimers, Trimers and Tetramers [data] Feb 20, 2024 - Gade Group Eichelmann, Robert; Ballmann, Joachim; Gade, Lutz H., 2024, "Tetraazacoronenes and Their Dimers, Trimers and Tetramers [data]", https://doi.org/10.11588/data/ZT3AHN, heiDATA, V1 Tetraazacoronenes were synthesized from bay-functionalized tetraazaperylenes by Zr-mediated cyclization and four-fold Suzuki–Miyaura cross coupling. In the Zr-mediated approach, an η4-cyclobutadiene-zirconium(IV) complex was isolated as an intermediate to cyclobutene-annulated de...
Band Formation at Interfaces Between N-Heteropolycycles and Gold Electrodes [research data] Feb 12, 2024 - SFB 1249: N-Heteropolyzyklen als Funktionsmaterialien - B: Theory & Structure Stein, Arnulf; Rolf, Daniela; Lotze, Christian; Günther, Benjamin; Gade, Lutz H.; Franke, Katharina J.; Tegeder, Petra, 2024, "Band Formation at Interfaces Between N-Heteropolycycles and Gold Electrodes [research data]", https://doi.org/10.11588/data/QNAPNN, heiDATA, V1 Underlying data for figures in the paper "Band Formation at Interfaces Between N-Heteropolycycles and Gold Electrodes"
Nanoscale flexible organic thin-film transistors [data] Feb 9, 2024 - SFB 1249: N-Heteropolyzyklen als Funktionsmaterialien - C: Material & Function Klauk, Hagen; Zschieschang, Ute; Waizmann, Ulrike; Weis, Jürgen; Borchert, James W., 2024, "Nanoscale flexible organic thin-film transistors [data]", https://doi.org/10.11588/data/7JALYI, heiDATA, V1 Direct-write electron-beam lithography has been used to fabricate low-voltage p-channel and n-channel organic thin-film transistors with channel lengths as small as 200 nm and gate-to-contact overlaps as small as 100 nm on glass and on flexible transparent polymeric substrates. T...
Stable Azaheptacenes Feb 1, 2024 - Bunz Group Zong, Wansheng; Hippchen, Nikolai; Nico, Zeitter; Maier, Steffen; Philipp, Ludwig; Rominger, Frank; Freudenberg, Jan; Bunz, Uwe H. F., 2024, "Stable Azaheptacenes", https://doi.org/10.11588/data/P9AVCU, heiDATA, V1 we have developed a novel access to stable azaheptacenes and investigated both their (air-stable) radical anions as well as dianions. The two azaheptacenes are significantly more stable than reported examples. We identified their structure through NMR, IR, MS and X-ray crystallog...
Facile two-step Synthesis of para-Dithienopyrazines [data] Jan 31, 2024 - SFB 1249: N-Heteropolyzyklen als Funktionsmaterialien - A: Synthesis Hashmi, A. Stephen K.; Hüßler, Christopher; Kahle, Justin; Dietl, Martin C.; Krämer, Petra; Rominger, Frank; Rudolph, Matthias, 2024, "Facile two-step Synthesis of para-Dithienopyrazines [data]", https://doi.org/10.11588/data/14RXKL, heiDATA, V1 N-Heteropolycyclic compounds are valuable building blocks in organic electronic devices. In this work, a convenient route for the synthesis of para-dithienopyrazines from readily available starting materials is described. A cascade of nucleophilic aromatic substitution and subseq...
Stabilization of Acenes: “Geländer”-Pentacenes [data] Jan 25, 2024 - Bunz Group Ludwig, Philipp; Rominger, Frank; Freudenberg, Jan; Bunz, Uwe H. F., 2024, "Stabilization of Acenes: “Geländer”-Pentacenes [data]", https://doi.org/10.11588/data/NITIKZ, heiDATA, V1 We report soluble tetrakis-biphenyl substituted pentacenes comprised of sp2 carbons and synthesized from pentacene-5,7,12,14-tetraone. Intramolecular Yamamoto coupling of two tetrakis(chlorobiphenylyl)pentacenes yields helical, doubly wrapped pentacenes, in which the quaterphenyl...
Pentacene to Octacene: The Limit of Fourfold TIPS-Ethynylation [data] Jan 22, 2024 - Bunz Group Zeitter, Nico; Hippchen, Nikolai; Baur, Philipp; Unterreiner, Tamara; Freudenberg, Jan; Rominger, Frank; Bunz, Uwe, 2024, "Pentacene to Octacene: The Limit of Fourfold TIPS-Ethynylation [data]", https://doi.org/10.11588/data/DDJFGS, heiDATA, V1 Soluble acenes beyond hexacene are rare. Their sensitivity complicates isolation, purification and application in devices. To increase the stability of acenes, functionalization with trialkylsilylethynyl substituents prevents [4+4] dimerization and oxidation. At the same time suc...
Halogenated Phenazinothiadiazoles: Electron Transporting Materials [data] Jan 8, 2024 - Bunz Group Zong, Wansheng; Hippchen, Nikolai; Dittmar, Benedikt; Elter, Maximilian; Ludwig, Philipp; Rominger, Frank; Freudenberg, Jan; Bunz, Uwe H. F., 2024, "Halogenated Phenazinothiadiazoles: Electron Transporting Materials [data]", https://doi.org/10.11588/data/PKX5CI, heiDATA, V1, UNF:6:M6UVaar224tmBy3Sj1o9jg== [fileUNF] Triisopropylsilyl-(TIPS)-alkynylated phenazinothiadiazoles were prepared by the condensation of halogenated ortho-quinones and TIPS-alkynylated 5,6-diamino-2,1,3-benzothiadiazole with different combinations of halogen substituents. The compounds pack in brickwall motif of head-to...

Zipping up Tetraazaperylene: Synthesis of Tetraazacoronenes via Double Coupling in the Bay Positions [data]

Feb 20, 2024 - Gade Group

Eichelmann, Robert; Rippel, Daniel; Ballmann, Joachim; Gade, Lutz H., 2024, "Zipping up Tetraazaperylene: Synthesis of Tetraazacoronenes via Double Coupling in the Bay Positions [data]", https://doi.org/10.11588/data/HIERR9, heiDATA, V1

Substituted tetraazacoronene fluorophores have been obtained selectively by double Suzuki–Miyaura cross coupling of symmetrically substituted 1,2-bis(pinacolatoboryl)alkenes with a bay-substituted octaazaperopyrenedioxide (OAPPDO). Subsequent Scholl reaction of the dimethoxypheny...

Chiral Bay-Alkynylated Tetraazaperylenes: Photophysics and Chiroptical Properties

Feb 20, 2024 - Gade Group

Eichelmann, Robert; Jeudy, Pierre; Schneider, Lars; Zerhoch, Jonathan; Mayer, Paula R.; Ballmann, Joachim; Deschler, Felix; Gade, Lutz H., 2024, "Chiral Bay-Alkynylated Tetraazaperylenes: Photophysics and Chiroptical Properties", https://doi.org/10.11588/data/PGSVXO, heiDATA, V1

Fully bay-alkynylated octaazaperopyrene dioxide (OAPPDO) derivatives were accessible through Stille cross coupling reaction of the corresponding bay-chlorinated derivatives. This steric congestion of the bay area led to helically chiral fluorophores, and chiral resolution of two...

Tetraazacoronenes and Their Dimers, Trimers and Tetramers [data]

Feb 20, 2024 - Gade Group

Eichelmann, Robert; Ballmann, Joachim; Gade, Lutz H., 2024, "Tetraazacoronenes and Their Dimers, Trimers and Tetramers [data]", https://doi.org/10.11588/data/ZT3AHN, heiDATA, V1

Tetraazacoronenes were synthesized from bay-functionalized tetraazaperylenes by Zr-mediated cyclization and four-fold Suzuki–Miyaura cross coupling. In the Zr-mediated approach, an η4-cyclobutadiene-zirconium(IV) complex was isolated as an intermediate to cyclobutene-annulated de...

Band Formation at Interfaces Between N-Heteropolycycles and Gold Electrodes [research data]

Feb 12, 2024 - SFB 1249: N-Heteropolyzyklen als Funktionsmaterialien - B: Theory & Structure

Stein, Arnulf; Rolf, Daniela; Lotze, Christian; Günther, Benjamin; Gade, Lutz H.; Franke, Katharina J.; Tegeder, Petra, 2024, "Band Formation at Interfaces Between N-Heteropolycycles and Gold Electrodes [research data]", https://doi.org/10.11588/data/QNAPNN, heiDATA, V1

Underlying data for figures in the paper "Band Formation at Interfaces Between N-Heteropolycycles and Gold Electrodes"

Nanoscale flexible organic thin-film transistors [data]

Feb 9, 2024 - SFB 1249: N-Heteropolyzyklen als Funktionsmaterialien - C: Material & Function

Klauk, Hagen; Zschieschang, Ute; Waizmann, Ulrike; Weis, Jürgen; Borchert, James W., 2024, "Nanoscale flexible organic thin-film transistors [data]", https://doi.org/10.11588/data/7JALYI, heiDATA, V1

Direct-write electron-beam lithography has been used to fabricate low-voltage p-channel and n-channel organic thin-film transistors with channel lengths as small as 200 nm and gate-to-contact overlaps as small as 100 nm on glass and on flexible transparent polymeric substrates. T...

Stable Azaheptacenes

Feb 1, 2024 - Bunz Group

Zong, Wansheng; Hippchen, Nikolai; Nico, Zeitter; Maier, Steffen; Philipp, Ludwig; Rominger, Frank; Freudenberg, Jan; Bunz, Uwe H. F., 2024, "Stable Azaheptacenes", https://doi.org/10.11588/data/P9AVCU, heiDATA, V1

we have developed a novel access to stable azaheptacenes and investigated both their (air-stable) radical anions as well as dianions. The two azaheptacenes are significantly more stable than reported examples. We identified their structure through NMR, IR, MS and X-ray crystallog...

Facile two-step Synthesis of para-Dithienopyrazines [data]

Jan 31, 2024 - SFB 1249: N-Heteropolyzyklen als Funktionsmaterialien - A: Synthesis

Hashmi, A. Stephen K.; Hüßler, Christopher; Kahle, Justin; Dietl, Martin C.; Krämer, Petra; Rominger, Frank; Rudolph, Matthias, 2024, "Facile two-step Synthesis of para-Dithienopyrazines [data]", https://doi.org/10.11588/data/14RXKL, heiDATA, V1

N-Heteropolycyclic compounds are valuable building blocks in organic electronic devices. In this work, a convenient route for the synthesis of para-dithienopyrazines from readily available starting materials is described. A cascade of nucleophilic aromatic substitution and subseq...

Stabilization of Acenes: “Geländer”-Pentacenes [data]

Jan 25, 2024 - Bunz Group

Ludwig, Philipp; Rominger, Frank; Freudenberg, Jan; Bunz, Uwe H. F., 2024, "Stabilization of Acenes: “Geländer”-Pentacenes [data]", https://doi.org/10.11588/data/NITIKZ, heiDATA, V1

We report soluble tetrakis-biphenyl substituted pentacenes comprised of sp2 carbons and synthesized from pentacene-5,7,12,14-tetraone. Intramolecular Yamamoto coupling of two tetrakis(chlorobiphenylyl)pentacenes yields helical, doubly wrapped pentacenes, in which the quaterphenyl...

Pentacene to Octacene: The Limit of Fourfold TIPS-Ethynylation [data]

Jan 22, 2024 - Bunz Group

Zeitter, Nico; Hippchen, Nikolai; Baur, Philipp; Unterreiner, Tamara; Freudenberg, Jan; Rominger, Frank; Bunz, Uwe, 2024, "Pentacene to Octacene: The Limit of Fourfold TIPS-Ethynylation [data]", https://doi.org/10.11588/data/DDJFGS, heiDATA, V1

Soluble acenes beyond hexacene are rare. Their sensitivity complicates isolation, purification and application in devices. To increase the stability of acenes, functionalization with trialkylsilylethynyl substituents prevents [4+4] dimerization and oxidation. At the same time suc...

Halogenated Phenazinothiadiazoles: Electron Transporting Materials [data]

Jan 8, 2024 - Bunz Group

Zong, Wansheng; Hippchen, Nikolai; Dittmar, Benedikt; Elter, Maximilian; Ludwig, Philipp; Rominger, Frank; Freudenberg, Jan; Bunz, Uwe H. F., 2024, "Halogenated Phenazinothiadiazoles: Electron Transporting Materials [data]", https://doi.org/10.11588/data/PKX5CI, heiDATA, V1, UNF:6:M6UVaar224tmBy3Sj1o9jg== [fileUNF]

Triisopropylsilyl-(TIPS)-alkynylated phenazinothiadiazoles were prepared by the condensation of halogenated ortho-quinones and TIPS-alkynylated 5,6-diamino-2,1,3-benzothiadiazole with different combinations of halogen substituents. The compounds pack in brickwall motif of head-to...

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