Synthesis, Crystal Structure, and Polymerization of 1,2:5,6:9,10-Tribenzo-3,7,11,13-tetradehydro[14]annulene

Baldwin, Kyle P.; Matzger, Adam J.; Scheiman, Daniel A.; Tessier, Claire A.; Vollhardt, K. Peter C.; Youngs, Wiley J.

doi:10.1055/s-1995-5247

Cited by 88 publications

(101 citation statements)

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“…The topochemical polymerization of a cyclic system is first achieved by Vollhardt, Youngs, and coworkers for crystals of octadehydrotribenzo [14]annulene in 1995. 30 Subsequently, construction of 1D-stacked assemblies and their topochemical polymerization were reported by Shimizu's, 29a Lauher's, 29d and Morin's 29e groups.…”

Section: Resultsmentioning

confidence: 99%

Effects of ortho-Phenyl Substitution on Molecular Arrangements of Octadehydrodibenzo[12]annulene

Hisaki

Manabe

Osaka

et al. 2013

Bulletin of the Chemical Society of Japan

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To modulate assembly manners of octadehydrodibenzo [12]annulene ([12]DBA) core in solid state, we first synthesized ortho-phenyl-substituted derivative 2 and investigated the effects of the substituents on the molecular stacking manner of the [12]DBA core.[12]DBA 2 yielded four types of crystals, which differ from that of the parent compound: Namely, the guest-free crystal possessing an offset stacking manner (I-GF), the solvate with a edge-to-face arrangement (II), the solvates with zigzag π-stacked arrangements (III and III¤), and the solvate with 1D π-stacked columnar arrangements (IV). In the crystals, the phenyl groups contribute to limiting the stacking geometry of the [12]DBA cores and to forming void spaces accommodating various guest species, allowing versatile molecular assembly manners hitherto known for [12]DBA derivatives. We revealed that the crystals showed structure dependent fluorescence and charge carrier behaviors.

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Section: Resultsmentioning

confidence: 99%

Effects of ortho-Phenyl Substitution on Molecular Arrangements of Octadehydrodibenzo[12]annulene

Hisaki

Manabe

Osaka

et al. 2013

Bulletin of the Chemical Society of Japan

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“…Figure 5 compares the electronic absorption spectra of ortho PC/DBA 5, its precursor 14 and dehydrobenzo [14]annulene (31). [20] A significant bathochromic shift (Dl % 60 nm) is observed relative to 14, indicating conjugation in the [14]annulene unit. Compared with 31, PC/DBA 5 shows a bathochromic shift of % 15 nm, which can be explained by through-space interactions in the cyclophane moiety.…”

Section: Pd-catalyzed Cross-coupling Of 45-diethynyl-a C H T U N G Tmentioning

confidence: 98%

Phane Properties of [2.2]Paracyclophane/Dehydrobenzoannulene Hybrids

Hinrichs

Boydston

Jones

et al. 2006

Chemistry A European J

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A series of [2.2]paracyclophane/dehydrobenzo[14]annulene (PC/DBA) hybrids (hydrocarbons 5, 6, 9, 10 b, and 10 c), [2.2]paracyclophane/dehydro[14]annulene (PC/DA) hybrids (7 and 8) and suitable model systems (11, 12, and 33) has been synthesized. Comparison of the electronic absorption spectra in each series of compounds provides further insight into the global communication between the decks in the [2.2]paracyclophane unit.

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“…[20] As described in the introduction, attempted topochemical polymerization of DBA derivatives in the crystalline state has not been successful. [27,29] On the other hand, in view of the high reactivity of DBA 1 b toward a transannular reaction, [26] we envisioned that, in two-dimensionally aligned DBAs, such as 1, topochemical polymerization would occur involving both butadiyne units in a molecule with transannular bond formation to yield peri-benzopolyacene 4 (see Scheme 1) with a fluoranthene substructure. A structural subunit of this polymer, rubicene (5), has been known for over 100 years (Figure 3 a).…”

Section: Resultsmentioning

confidence: 99%

“…[28] In the stacked geometry of DBAs in crystals, the butadiyne units in a DBA molecule are expected to polymerize individually to form poly(butadiyne) moieties in the resultant tubular polymers. [29] Contrary to polymerization, Swager et al also reported the formation of tetraiododibenzoindacene derivative 2 upon treatment of 1 b with iodine through transannular bond formation. Though the mechanism of this reaction is not certain, one may speculate tetraradical intermediate 3 formed by spontaneous transannular bond formation in 1 b, similar to the formation of the 1,4-benzene diradical generated by a Bergman reaction.…”

Section: A C H T U N G T R E N N U N G Atomic Distance Between the Dimentioning

confidence: 99%

Self‐Assembled Monolayers of Alkoxy‐Substituted Octadehydrodibenzo[12]annulenes on a Graphite Surface: Attempts at peri‐Benzopolyacene Formation by On‐Surface Polymerization

Tahara

Inukai

Hara

et al. 2010

Chemistry A European J

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Self-assembled monolayers of a series of tetraalkoxy-substituted octadehydrodibenzo[12]annulene (DBA) derivatives 1c-g possessing butadiyne linkages were studied at the 1,2,4-trichlorobenzene (TCB) or 1-phenyloctane/graphite interface by scanning tunneling microscopy (STM). The purpose of this research is not only to investigate the structural variation of two-dimensional (2D) monolayers, but also to assess a possibility for peri-benzopolyacene formation by two-dimensionally controlled polymerization on a surface. As a result, the formation of three structures, porous, linear, and lamella structures, were observed by changing the alkyl chain length and the solute concentration. The formation of multilayers of the lamella structure was often observed for all compounds. The selection of molecular networks is basically ascribed to intermolecular and molecule-substrate interactions per unit area and network density. The selective appearance of the linear structure of 1d is attributed to favorable epitaxial registry matching between the substrate lattice and the overlayer lattice. Even though the closest interatomic distance between the diacetylenic units of the DBAs in the lamella structure (approximately 0.6 nm) is slightly larger compared to the typical distances necessary for topochemical polymerization, the reactivity toward external stimuli (electronic-pulse irradiation from an STM tip and UV irradiation) was investigated. Unfortunately, no evidence for polymerization of the DBAs on the surface was observed. The present results indicate the necessity for further designing a suitable system for the on-surface construction of structurally novel conjugated polymers, which are otherwise difficult to prepare.

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Synthesis, Crystal Structure, and Polymerization of 1,2:5,6:9,10-Tribenzo-3,7,11,13-tetradehydro[14]annulene

Cited by 88 publications

References 0 publications

Effects of ortho-Phenyl Substitution on Molecular Arrangements of Octadehydrodibenzo[12]annulene

Effects of ortho-Phenyl Substitution on Molecular Arrangements of Octadehydrodibenzo[12]annulene

Phane Properties of [2.2]Paracyclophane/Dehydrobenzoannulene Hybrids

Self‐Assembled Monolayers of Alkoxy‐Substituted Octadehydrodibenzo[12]annulenes on a Graphite Surface: Attempts at peri‐Benzopolyacene Formation by On‐Surface Polymerization

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