Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene

• Long K. San,
• Sebastian Balser,
• Brian J. Reeves,
• Tyler T. Clikeman,
• Yu-Sheng Chen,
• Steven H. Strauss and
• Olga V. Boltalina

Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39

• photostability compared to ANTH and 9,10-ANTH derivatives, and a simple synthetic access makes it an attractive material as a deep-blue OLED emitter and an efficient fluorescent probe. Keywords: anthracene; dibromoanthracene; electron poor polyaromatic systems; fluorescence; perfluoroalkylation

• . Experimental Solvents and reagents The following reagents and solvents were used as received unless otherwise indicated: anthracene (TCI America, 94%); 9,10-dibromoanthracene (Thermo Scientific Chemicals, 98%); heptafluorobenzyl iodide (C6F5CF2I, SynQuest, 90%); cyclohexane (Mallinckrodt); 1,4‐bis

Biphenylene-containing polycyclic conjugated compounds

• Cagatay Dengiz

Beilstein J. Org. Chem. 2023, 19, 1895–1911, doi:10.3762/bjoc.19.141

• researchers efficiently conducted palladium-catalyzed C–H activated annulation reactions, involving oxanorbornadiene derivative 26 and aryl bromides including dibromoanthracene 27 [38]. Subsequent aromatization reactions were then carried out, resulting in the successful synthesis of the target POAs with high

• via [2 + 2] and [2 + 2 + 2] cycloadditions. In a closely related study conducted by Grill et al., the behavior of 2,3-dibromoanthracene (89) was examined on two distinct surfaces [Au(100) and Au(111)] (Scheme 19) [52]. Notably, on the Au(111) substrate, nearly equivalent quantities of dimer 91

Towards triptycene functionalization and triptycene-linked porphyrin arrays

• Gemma M. Locke,
• Keith J. Flanagan and
• Mathias O. Senge

Beilstein J. Org. Chem. 2020, 16, 763–777, doi:10.3762/bjoc.16.70

• [34] directly through various Pd-catalyzed or organocopper cross-coupling [35] reactions. However, exploratory studies did not show much promise and this approach was abandoned, as was the functionalization of 9,10-dibromoanthracene with phenyl spacers prior to triptycene formation (see Supporting

Self-assembled coordination thioether silver(I) macrocyclic complexes for homogeneous catalysis

• Zhen Cao,
• Aline Lacoudre,
• Cybille Rossy and
• Brigitte Bibal

Beilstein J. Org. Chem. 2019, 15, 2465–2472, doi:10.3762/bjoc.15.239

• reactions of alkynes. Results and Discussion Synthesis of silver(I) complexes Ligand 1 was synthesized in one step, from commercially available 9,10-dibromoanthracene and 2-(methylthio)phenylboronic acid, using a Suzuki–Miyaura cross-coupling reaction. Notably, the yield was low (26%) [55], and the X-ray

Functionalization of anthracene: A selective route to brominated 1,4-anthraquinones

• Kiymet Berkil Akar,
• Osman Cakmak,
• Orhan Büyükgüngör and
• Ertan Sahin

Beilstein J. Org. Chem. 2011, 7, 1036–1045, doi:10.3762/bjoc.7.118

• -dione (28). Therefore a selective and efficient method was developed for the preparation of compound 28 starting from 9,10-dibromoanthracene (1), in a simple four-step process. Compounds 10 and 11, and diol 27 constitute key precursors for the preparation of functionalized substituted anthracene

• substitution; Introduction Our sustained interest in benzenoid aromatic compounds with high bromine content has led to the development of a regio- and stereoselective bromination method for aromatic compounds. Recently, we demonstrated the selective bromination of 9,10-dibromoanthracene (1) to give

• this work, we report on new methoxy and hydroxy derivatives of anthracene, whose further transformation generates synthetically important novel anthracene derivatives. We also report an effective synthetic route to 1,4-dione 28 starting from 9,10-dibromoanthracene (1) in four steps. The compounds

Highly brominated anthracenes as precursors for the convenient synthesis of 2,9,10-trisubstituted anthracene derivatives

• Osman Cakmak,
• Leyla Aydogan,
• Kiymet Berkil,
• Ilhami Gulcin and
• Orhan Buyukgungor

Beilstein J. Org. Chem. 2008, 4, No. 50, doi:10.3762/bjoc.4.50

• , Faculty of Art and Science, Department of Physics, TR-55060, Samsun, Turkey (author to whom inquries concerning the X-ray structure should be directed) 10.3762/bjoc.4.50 Abstract When 9,10-dibromoanthracene was treated with bromine in CCl4 without a catalyst, 1,2,3,4,9,10-hexabromo-1,2,3,4

• difficult to prepare by other routes [24]. On the other hand, in a previous study, we isolated stereoisomeric hexabromide 3 from a complex reaction mixture of photobromination of 9,10-dibromoanthracene (2) in which the structure of 3 was established by X-ray analysis [25]. We now wish to report on the

• demonstrated that the bromination conditions of 9,10-dibromoanthracene dramatically affect the nature of the stereoisomeric hexabromide product and ratio. The studies also revealed that aromatization of hexabromide 3 depends strongly on the choice of base. Experimental General Thin layer chromatography was

Synthesis of 2,3,6,7-tetrabromoanthracene

• Christian Schäfer,
• Friederike Herrmann and
• Jochen Mattay

Beilstein J. Org. Chem. 2008, 4, No. 41, doi:10.3762/bjoc.4.41

• and Chou presented the first synthesis of 2,3-dibromoanthracene [5], using a Diels-Alder reaction as the key step in synthesis. Twelve years later, Bowles and Anthony published an alternative synthesis for the same compound using a Bergman cyclization [6]. There are several other publications