Dataset Information

Three-Dimensional Pyrene-Fused N-Heteroacenes.

ABSTRACT: Four three-dimensional (3D) pyrene-fused N-heteroacenes (P1-P4) are designed and synthesized. From P1 to P4, their lengths are extended in an iterative way, where the thiadiazole unit can be reduced to diamine and the obtained diamines can be further condensed with the diketones with a thiadiazole unit. Compared to their two-dimensional counterparts, the solubility of these 3D pyrene-fused N-heteroacenes is improved by this 3D covalent linkage with two-dimensional units. The diameters of P1-P4 are 3.66, 6.06, 8.48 and 10.88 nm, respectively, and these 3D molecules are characterized by ¹H, ¹³C and 2D NMR, MS, UV-vis, PL and CV spectra. Our strategy shows a promising way to large 3D pyrene-fused N-heteroacenes.

SUBMITTER: Hu BL

PROVIDER: S-EPMC6727623 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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Three-Dimensional Pyrene-Fused N-Heteroacenes.

Hu Ben-Lin BL An Cunbin C Wagner Manfred M Ivanova Georgia G Ivanova Anela A Baumgarten Martin M

Journal of the American Chemical Society 20190318 13

Four three-dimensional (3D) pyrene-fused N-heteroacenes (P1-P4) are designed and synthesized. From P1 to P4, their lengths are extended in an iterative way, where the thiadiazole unit can be reduced to diamine and the obtained diamines can be further condensed with the diketones with a thiadiazole unit. Compared to their two-dimensional counterparts, the solubility of these 3D pyrene-fused N-heteroacenes is improved by this 3D covalent linkage with two-dimensional units. The diameters of P1-P4 a ...[more]

PMID: 30860825

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Project description:π-Extended pyrene compounds possess remarkable luminescent and semiconducting properties and are being intensively investigated as electroluminescent materials for potential uses in organic light-emitting diodes, transistors, and solar cells. Here, the synthesis of two sets of pyrene-containing π-conjugated polyaromatic regioisomers, namely 2,3,10,11,14,15,20,21-octaalkyloxypentabenzo[a,c,m,o,rst]pentaphene (BBPn) and 2,3,6,7,13,14,17,18-octaalkyloxydibenzo[j,tuv]phenanthro [9,10-b]picene (DBPn), is reported. They were obtained using the Suzuki-Miyaura cross-coupling in tandem with Scholl oxidative cyclodehydrogenation reactions from the easily accessible precursors 1,8- and 1,6-dibromopyrene, respectively. Both sets of compounds, equipped with eight peripheral aliphatic chains, self-assemble into a single hexagonal columnar mesophase, with one short-chain BBPn homolog also exhibiting another columnar mesophase at a lower temperature, with a rectangular symmetry; BBPn isomers also possess wider mesophase ranges and higher mesophases' stability than their DBPn homologs. These polycyclic aromatic hydrocarbons all show a strong tendency of face-on orientation on the substrate and could be controlled to edge-on alignment through mechanical shearing of interest for their implementation in photoelectronic devices. In addition, both series BBPn and DBPn display green-yellow luminescence, with high fluorescence quantum yields, around 30%. In particular, BBPn exhibit a blue shift phenomenon in both absorption and emission with respect to their DBPn isomers. DFT results were in good agreement with the optical properties and with the stability ranges of the mesophases by confirming the higher divergence from the flatness of DBPn compared with BBPn. Based on these interesting properties, these isomers could be potentially applied not only in the field of fluorescent dyes but also in the field of organic photoelectric semiconductor materials as electron transport materials.

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Three-Dimensional Pyrene-Fused N-Heteroacenes.

Publications

Three-Dimensional Pyrene-Fused N-Heteroacenes.

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