Open Research Data from the Bunz Group at the Institute of Organic Chemistry of Heidelberg University.
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1 to 10 of 24 Results
Jun 5, 2024
Elter, Maximilian; Ahrens, Lukas; Luo, Stella M.; Rominger, Frank; Freudenberg, Jan; Cao, Dennis D.; Bunz, Uwe H. F., 2024, "Cata-Annulated Azaacene Bisimides [data]",, heiDATA, V1
Ultra-electron-deficient azaacenes were synthesized via Buchwald-Hartwig coupling of ortho-diaminoarenes with chlorinated mellophanic diimide followed by oxidation of the intermediate N,N’-dihydro compounds with MnO2 or PbO2. The resulting cata-annulated bisimide azaacenes have u...
May 27, 2024
Ahrens, Lukas; Tverskoy, Olena; Weigold, Svenja; Ganschow, Michael; Rominger, Frank; Freudenberg, Jan; Bunz, Uwe H. F., 2024, "(Aza)Pentacenes Clipped into a Ring: Stabilization of Large (Aza)Acenes [data]",, heiDATA, V1
A doubly alkylene bridged 6,13-diphenylpentacene and analogously bridged azapentacenes were prepared; they are persistent. The doubly bridged azapentacenes display superior photochemical, oxidative and thermal stabilities compared to azapentacenes protected by bis(TIPS-ethynyl)-s...
Mar 4, 2024
Ehjeij, Daniel; Rominger, Frank; Bunz, Uwe; Freudenberg, Jan; Müllen, Klaus, 2024, "Thermolysis of Biphenylene toward Cyclo-ortho-phenylenes [data]",, heiDATA, V1
The solvent and catalyst free thermolysis of biphenylenes at 350 °C furnishes [n]cyclo-ortho-phenylenes ([n]COPs, n=4–10) in one step and in high yields. At 400 °C biphenylene dimerizes into tetraphenylene, but lower reaction temperatures produce cyclooligomers. If suitably subst...
Feb 1, 2024
Zong, Wansheng; Hippchen, Nikolai; Nico, Zeitter; Maier, Steffen; Philipp, Ludwig; Rominger, Frank; Freudenberg, Jan; Bunz, Uwe H. F., 2024, "Stable Azaheptacenes",, 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...
Jan 25, 2024
Ludwig, Philipp; Rominger, Frank; Freudenberg, Jan; Bunz, Uwe H. F., 2024, "Stabilization of Acenes: “Geländer”-Pentacenes [data]",, 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...
Jan 22, 2024
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]",, 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...
Jan 8, 2024
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]",, 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...
Nov 3, 2023
Ludwig, Philipp; Mayer, Jacob; Ahrens, Lukas; Rominger, Frank; Ligorio, Giovanni; Hermerschmidt, Felix; List-Kratochvil, Emil J.W.; Freudenberg, Jan; Bunz, Uwe H.F., 2023, "Doubly Bridged Anthracenes: Blue Emitters for OLEDs [data]",, heiDATA, V1
The photooxidative stability of a series of doubly bridged anthracenes was evaluated after their preparation via twofold macrocyclization of a bis(resorcinyl)anthracene. Lightfastness correlates with the energy levels of the highest occupied molecular orbital (HOMO), resulting in...
Aug 8, 2023
Zeitter, Nico; Hippchen, Nikolai; Weidlich, Anna; Jäger, Patrick; Ludwig, Philipp; Dr. Rominger, Frank; Dr. Freudenberg, Jan; Prof. Dr. Dreuw, Andreas; Prof. Dr. Bunz, Uwe H. F, 2023, "Hexakis-TIPS-Alkynylated Nonacenes: Persistent and Processible [data]",, heiDATA, V1
We prepared and characterized (UV-vis, epr, X-ray) four substituted nonacenes. They are the most stable and soluble nonacenes to date – due to six strategically placed triisopropylsilyl (TIPS)-ethynyl groups. They are stable for several weeks in the solid state. In dilute solutio...
May 31, 2023
Fuchs, Kathleen; Dr. Rivero, Samara M.; Weidlich, Anna; Dr. Rominger, Frank; Israel, Noel; Dr. Popov, Alexey A.; Prof. Dreuw, Andreas; Dr. Freudenberg, Jan; Prof. Casado, Juan; Prof. Bunz, Uwe, 2023, "Dimerization of a Reactive Azaacene Diradical: Synthesis of a Covalent Azaacene Cage [Data]",, heiDATA, V1
Two series of regioisomeric dicyanomethylene substituted dithienodiazatetracenes with formal para- or ortho- quinodimethane subunits were synthesized and characterized. Whereas the para-isomers (p-n, diradical index y0=0.01) are stable and isolable, the ortho-isomer (y0=0.98) dim...
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