Synthesis of NewC3h andC3v Truxene Derivatives

Abstract

Palladium-catalyzed cross coupling of 2,7,12-tribromotruxene with organostannanes and boronic acids leads to 2,7,12trisubstituted truxenes. 5,10,15-Triarylated and trialkynylated truxene derivatives are obtained by the reaction of trux-Scheme 1 [a]

Toward an Air-Stable Triradical with Strong Spin Coupling: Synthesis of Substituted Truxene-5,10,15-triyl

“…In the literature, by producing the tri-anionic state of a substituted truxene, the diastereomer mixture could be converged to the all syn-configuration and thus greatly simplified the 1 H NMR spectrum. 50 Upon such an isomerization process, the 1 H NMR spectroscopy clearly confirmed the structure of syn-H-1-An (Supporting Information), by which the structure of H-1-An was substantiated. On the other hand, the results from these experiments also revealed that H-1′-An was not a diastereomer of H-1-An, as it was not convertible to syn-H-1-An.…”

“…In order to further elucidate the structures of H-1-An and H-1′-An , which constitute vital clues to the identity of the oxidation radical product, an isomerization protocol was conducted (Scheme ). In the literature, by producing the tri-anionic state of a substituted truxene, the diastereomer mixture could be converged to the all syn-configuration and thus greatly simplified the 1 H NMR spectrum . Upon such an isomerization process, the 1 H NMR spectroscopy clearly confirmed the structure of syn - H-1-An (Supporting Information), by which the structure of H-1-An was substantiated.…”

Toward an Air-Stable Triradical with Strong Spin Coupling: Synthesis of Substituted Truxene-5,10,15-triyl

“…In the literature, by producing the tri-anionic state of a substituted truxene, the diastereomer mixture could be converged to the all syn-configuration and thus greatly simplified the 1 H NMR spectrum. 50 Upon such an isomerization process, the 1 H NMR spectroscopy clearly confirmed the structure of syn-H-1-An (Supporting Information), by which the structure of H-1-An was substantiated. On the other hand, the results from these experiments also revealed that H-1′-An was not a diastereomer of H-1-An, as it was not convertible to syn-H-1-An.…”

“…In order to further elucidate the structures of H-1-An and H-1′-An , which constitute vital clues to the identity of the oxidation radical product, an isomerization protocol was conducted (Scheme ). In the literature, by producing the tri-anionic state of a substituted truxene, the diastereomer mixture could be converged to the all syn-configuration and thus greatly simplified the 1 H NMR spectrum . Upon such an isomerization process, the 1 H NMR spectroscopy clearly confirmed the structure of syn - H-1-An (Supporting Information), by which the structure of H-1-An was substantiated.…”

Effect of the Linkage Position on the Conjugation Length of Truxene-Based Porous Polymers: Implications for Their Sensing Performance of Nitroaromatics

“…The synthesis of the monomers 2,7,12-tribromohexamethyltruxene ( Tx2Br ) and 3,8,13-tribromohexamethyltruxene ( Tx3Br ) was performed in just two steps starting from commercially available 6- and 5-bromoindanone. Thus, cyclotrimerization of 6- and 5-bromoindanone mediated by p -toluenesulfonic and propionic acid cyclotrimerization rendered 2,7,12-tribromotruxene and 3,8,13-tribromotruxene, respectively. Subsequent treatment of truxenes with KO t Bu and alkylation with MeI yielded Tx2Br and Tx3Br in excellent yields.…”

Solvent‐Dependent Truxene‐Based Nanostructures

“…Synthesis and characterization of compounds : The synthesis of the three new compounds (Scheme ) was started from known tribromotruxene 13. Compound 2 is prepared in good yield by threefold Suzuki coupling of tribromotruxene with 4‐nonylbenzeneboronic acid in the presence of Pd(PPh 3 ) 4 and 2 M aqueous K 2 CO 3 with THF as solvent.…”

Toward an Air-Stable Triradical with Strong Spin Coupling: Synthesis of Substituted Truxene-5,10,15-triyl

“…In the literature, by producing the tri-anionic state of a substituted truxene, the diastereomer mixture could be converged to the all syn-configuration and thus greatly simplified the 1 H NMR spectrum. 50 Upon such an isomerization process, the 1 H NMR spectroscopy clearly confirmed the structure of syn-H-1-An (Supporting Information), by which the structure of H-1-An was substantiated. On the other hand, the results from these experiments also revealed that H-1′-An was not a diastereomer of H-1-An, as it was not convertible to syn-H-1-An.…”

“…In order to further elucidate the structures of H-1-An and H-1′-An , which constitute vital clues to the identity of the oxidation radical product, an isomerization protocol was conducted (Scheme ). In the literature, by producing the tri-anionic state of a substituted truxene, the diastereomer mixture could be converged to the all syn-configuration and thus greatly simplified the 1 H NMR spectrum . Upon such an isomerization process, the 1 H NMR spectroscopy clearly confirmed the structure of syn - H-1-An (Supporting Information), by which the structure of H-1-An was substantiated.…”

Effect of the Linkage Position on the Conjugation Length of Truxene-Based Porous Polymers: Implications for Their Sensing Performance of Nitroaromatics

“…The synthesis of the monomers 2,7,12-tribromohexamethyltruxene ( Tx2Br ) and 3,8,13-tribromohexamethyltruxene ( Tx3Br ) was performed in just two steps starting from commercially available 6- and 5-bromoindanone. Thus, cyclotrimerization of 6- and 5-bromoindanone mediated by p -toluenesulfonic and propionic acid cyclotrimerization rendered 2,7,12-tribromotruxene and 3,8,13-tribromotruxene, respectively. Subsequent treatment of truxenes with KO t Bu and alkylation with MeI yielded Tx2Br and Tx3Br in excellent yields.…”

Solvent‐Dependent Truxene‐Based Nanostructures

“…Synthesis and characterization of compounds : The synthesis of the three new compounds (Scheme ) was started from known tribromotruxene 13. Compound 2 is prepared in good yield by threefold Suzuki coupling of tribromotruxene with 4‐nonylbenzeneboronic acid in the presence of Pd(PPh 3 ) 4 and 2 M aqueous K 2 CO 3 with THF as solvent.…”

Toward an Air-Stable Triradical with Strong Spin Coupling: Synthesis of Substituted Truxene-5,10,15-triyl

“…In the literature, by producing the tri-anionic state of a substituted truxene, the diastereomer mixture could be converged to the all syn-configuration and thus greatly simplified the 1 H NMR spectrum. 50 Upon such an isomerization process, the 1 H NMR spectroscopy clearly confirmed the structure of syn-H-1-An (Supporting Information), by which the structure of H-1-An was substantiated. On the other hand, the results from these experiments also revealed that H-1′-An was not a diastereomer of H-1-An, as it was not convertible to syn-H-1-An.…”

“…In order to further elucidate the structures of H-1-An and H-1′-An , which constitute vital clues to the identity of the oxidation radical product, an isomerization protocol was conducted (Scheme ). In the literature, by producing the tri-anionic state of a substituted truxene, the diastereomer mixture could be converged to the all syn-configuration and thus greatly simplified the 1 H NMR spectrum . Upon such an isomerization process, the 1 H NMR spectroscopy clearly confirmed the structure of syn - H-1-An (Supporting Information), by which the structure of H-1-An was substantiated.…”

Effect of the Linkage Position on the Conjugation Length of Truxene-Based Porous Polymers: Implications for Their Sensing Performance of Nitroaromatics

“…The synthesis of the monomers 2,7,12-tribromohexamethyltruxene ( Tx2Br ) and 3,8,13-tribromohexamethyltruxene ( Tx3Br ) was performed in just two steps starting from commercially available 6- and 5-bromoindanone. Thus, cyclotrimerization of 6- and 5-bromoindanone mediated by p -toluenesulfonic and propionic acid cyclotrimerization rendered 2,7,12-tribromotruxene and 3,8,13-tribromotruxene, respectively. Subsequent treatment of truxenes with KO t Bu and alkylation with MeI yielded Tx2Br and Tx3Br in excellent yields.…”

Solvent‐Dependent Truxene‐Based Nanostructures

“…Synthesis and characterization of compounds : The synthesis of the three new compounds (Scheme ) was started from known tribromotruxene 13. Compound 2 is prepared in good yield by threefold Suzuki coupling of tribromotruxene with 4‐nonylbenzeneboronic acid in the presence of Pd(PPh 3 ) 4 and 2 M aqueous K 2 CO 3 with THF as solvent.…”