Copper‐Mediated Simple and Efficient Synthesis of Tribenzohexadehydro[12]annulene and Its Derivatives.

Iyoda, Masahiko; Sirinintasak, Siriwan; Nishiyama, Yoshihiro; Vorasingha, Anusorn; Sultana, Fatema; Nakao, Kazumi; Kuwatani, Yoshiyuki; Matsuyama, Haruo; Yoshida, Masato; Miyake, Yoshihiro

doi:10.1002/chin.200443098

Cited by 2 publications

(8 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For example, measured locations of the maximum intensity peaks are in the range 3.59-4.05 eV 5,46,48 Furthermore, measured locations of lowest energy peaks also exhibit significant variation in the range 2.55-3.40 eV. 5,46,48 On comparison of experimental results to our calculations ( The last graphyne substructure we discuss also has 42 carbon atoms and five benzene rings, but arranged in C 2v symmetry (see Fig. 1h).…”

Section: Experimental Valuesmentioning

confidence: 63%

“…GU-42-D 2h consists of five benzene rings and 42 carbon atoms in all, arranged in D 2h symmetry (see Figure 1g), and its hydrogen-saturated version also belongs to the DBA class. Iyoda et al, 48 Johnson et al, 46 and Kehoe et al 5 have reported the measurements of optical absorption spectra of this compound, fully or partially saturated by hydrogens. However, there is a very significant difference among the results of these experiments, as far as peak locations are concerned.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Iyoda et al, 48 Johnson et al, 46 and Kehoe et al 5 have reported the measurements of optical absorption spectra this compound, fully, or partially, saturated by hydrogens. However, there is very significant difference among the results of these experiments, as far as peak locations are concerned.…”

Section: Experimental Valuesmentioning

confidence: 99%

“…A large number of measurements of optical absorption spectra of hydrocarbons, which are structural analogues of GUs, have been reported in the literature. 3,5,15,[40][41][42][43][44][45][46][47][48] Hydrocarbon analogue of GU-24 (Fig. 1e) is tribenzo [12]annulene, whose UV-Vis spectrum was first measured by Campbell et al 44 , and later on by several other workers.…”

Section: Absorption Spectra Of Graphyne Substructuresmentioning

confidence: 99%

See 3 more Smart Citations

Tunable Optoelectronic Properties of Triply Bonded Carbon Molecules with Linear and Graphyne Substructures

2018

View full text Add to dashboard Cite

In this paper we present a detailed computational study of the electronic structure and optical properties of triply-bonded hydrocarbons with linear, and graphyne substructures, with the aim of identifying their potential in opto-electronic device applications. For the purpose, we employed a correlated electron methodology based upon the Pariser-Parr-Pople model Hamiltonian, coupled with the configuration interaction (CI) approach, and studied structures containing up to 42 carbon atoms.Our calculations, based upon large-scale CI expansions, reveal that the linear structures have intense optical absorption at the HOMO-LUMO gap, while the graphyne ones have those at higher energies. Thus, the opto-electronic properties depend on the topology of the graphyne substructures, suggesting that they can be tuned by means of structural modifications. Our results are in very good agreement with the available experimental data.

show abstract

Section: Experimental Valuesmentioning

confidence: 63%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Experimental Valuesmentioning

confidence: 99%

Section: Absorption Spectra Of Graphyne Substructuresmentioning

confidence: 99%

See 2 more Smart Citations

Tunable Optoelectronic Properties of Triply Bonded Carbon Molecules with Linear and Graphyne Substructures

2018

View full text Add to dashboard Cite

show abstract

“…19,37,38 Parent DBA and hexakis(phenylethynyl)benzene were synthesized according to previous reports. 39,40 Commercially available tetradecane (TCI) was used for STM experiments. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 9 All STM experiments were performed at 20-26 °C using a Nanoscope IIIa or IIID (Bruker AXS) with an external pulse/function generator (Agilent 33220A).…”

Section: Methodsmentioning

confidence: 99%

Formation of Multicomponent Star Structures at the Liquid/Solid Interface

et al. 2015

View full text Add to dashboard Cite

To demonstrate key roles of multiple interactions between multiple components and multiple phases in the formation of an uncommon self-assembling pattern, we present here the construction of a porous hexagonal star (h-star) structure using a trigonal molecular building block at the liquid/solid interface. For this purpose, self-assembly of hexaalkoxy-substituted dehydrobenzo[12]annulene derivatives DBA-OCns was investigated at the tetradecane/graphite interface by means of scanning tunneling microscopy (STM). Monolayer structures were significantly influenced by coadsorbed tetradecane molecules depending on the alkyl chains length (C13-C16) of DBA-OCn. However, none of DBA-OCn molecules formed the expected trigonal complexes, indicating that an additional driving force is necessary for the formation of the trigonal complex and its assembly into the h-star structure. As a first approach, we employed the "guest induced structural change" for the formation of the h-star structure. In the presence of two guest molecules, nonsubstituted DBA and hexakis(phenylethynyl)benzene which fit the respective pores, an h-star structure was formed by DBA-OC15 at the tetradecane/graphite interface. Moreover, a tetradecane molecule was coadsorbed between a pair of alkyl chains of DBA-OC15, thereby blocking the interdigitation of the alkyl chain pairs. Therefore, the h-star structure results from the self-assembly of the four molecular components including the solvent molecule. The second approach is based on aggregation of perfluoroalkyl chains via fluorophilicity of DBA-F, in which the perfluoroalkyl groups are substituted at the end of three alkyl chains of DBA-OCn via p-phenylene linkers. A trigonal complex consisting of DBA-F and three tetradecane molecules formed an h-star structure, in which the perfluoroalkyl groups that orient into the alkane solution phase aggregated at the hexagonal pore via fluorophilicity. The present result provides useful insight into the design and control of complex molecular self-assembly at the liquid/solid interface.

show abstract

Copper‐Mediated Simple and Efficient Synthesis of Tribenzohexadehydro[12]annulene and Its Derivatives.

Cited by 2 publications

References 1 publication

Tunable Optoelectronic Properties of Triply Bonded Carbon Molecules with Linear and Graphyne Substructures

Tunable Optoelectronic Properties of Triply Bonded Carbon Molecules with Linear and Graphyne Substructures

Formation of Multicomponent Star Structures at the Liquid/Solid Interface

Contact Info

Product

Resources

About