A triazine-based three-directional rigid-rod tecton forms a novel 1D channel structure

Ranganathan, Anupama; Heisen, Burkhard Clemens; Dix, Ina; Meyer, Franc

doi:10.1039/b706627a

Cited by 51 publications

(44 citation statements)

References 37 publications

(17 reference statements)

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“…The trifluoromethane sulfonic acid catalyzed cyclotrimerization of p -bromobenzonitrile 97c to 2,4,6-tris-4-bromophenyl-1,3,5-triazine 98h has become a key step in the preparation of stars with a 1,3,5-triazine core [275,282,283,284,285]. …”

Section: Compounds With Heterocyclic Coresmentioning

confidence: 99%

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Star-Shaped Conjugated Systems

2010

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The present review deals with the preparation and the properties of star-shaped conjugated compounds. Three, four or six conjugated arms are attached to cross-conjugated cores, which consist of single atoms (B, C+, N), benzene or azine rings or polycyclic ring systems, as for example triphenylene or tristriazolotriazine. Many of these shape-persistent [n]star compounds tend to π-stacking and self-organization, and exhibit interesting properties in materials science: Linear and non-linear optics, electrical conductivity, electroluminescence, formation of liquid crystalline phases, etc.

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Section: Compounds With Heterocyclic Coresmentioning

confidence: 99%

“…The stepwise approach (coupling with TMS-acetylene to 109a (E = TMS), deprotection to tris(ethynylphenyl)-1,3,5-triazine 109b (E = H) and second coupling of the deprotected star with iodoarenes [282] as well as the direct coupling with phenylacetylenes 110a-g [283,284,285] have been used (Scheme 28). …”

Section: Compounds With Heterocyclic Coresmentioning

confidence: 99%

Star-Shaped Conjugated Systems

2010

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“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] Such structural features can, alternatively, be assembled from molecular tectonics, a concept first introduced by Wuest et al in 1991 [18] that offers an avenue for the bottom-up fabrication from small molecules by means of their spatially tailored, directional, and selective interactions between nearest neighbors. [19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38] Available interactions employed in the design of tectonic assembly include van der Waals forces, [39] electrostatic attraction, [40] p-p stacking, [41] hydrogen bonding, [27][28][29][30][31][32][33]…”

Section: Introductionmentioning

confidence: 99%

Oligomeric Tectonics: Supramolecular Assembly of Double‐Stranded Oligobisnorbornene through π–π Stacking

Lee

Lin

Liao

et al. 2009

Chemistry A European J

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Self-assembly at the molecular level in solutions or on a surface is a subject of current interest. Herein we describe the tailoring of oligobisnorbornene 1, which represents an innovative concept of a preorganized building block on the tens of nanometer scale. The rodlike 1 has vinyl and styrenyl end groups. Scanning tunneling microscopy (STM) reveals that the oligomers aggregate anisotropically along the long axis and form a one-dimensional assembly in which, remarkably, no interstitial gap appears between neighboring oligomers. Dynamic light-scattering (DLS) measurements indicate that the assembly develops in solution. With a shear treatment for dropcast films, a unidirectionally ordered domain with a defect density less than 0.5 % can be prepared. Simulation results by molecular dynamics suggest that there may be multiple interactions such as pi-pi stacking and dipolar attractions taking place between the termini of the oligomers. To demonstrate the importance of double bonds in the oligomeric backbones and termini towards the tectonic assembly, a hydrogenated analogue was synthesized; pi-pi interactions are thus less significant and the film morphology is completely different from that of 1. This work extends the concept of molecular tectonics to preorganized oligomers and opens up a new avenue of nanopatterning toward nanodevices.

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“…While the room-temperature trimerization of similar arylnitriles to 1,3,5-triazines using triflic acid is known, 29,30 heating is required to trimerize compound 1. The syntheses of pyridyl analogs of tris-(dFB)Tz were also attempted; however, numerous trimerization reaction conditions failed to give the desired compounds.…”

Section: Synthesis Tris-(dfb)tzmentioning

confidence: 99%

Blue phosphorescent organic light-emitting devices utilizing cesium–carbonate-doped 2,4,6-tris(2′,4′-difluoro-[1,1′-biphenyl]-4-yl)-1,3,5-triazine

Swensen

2011

J. Photon. Energy

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Abstract. We report an alternative, high-yielding synthesis for the known compound 2,4,6-tris(2 ,4 -difluoro-[1,1 -biphenyl]-4-yl)-1,3,5-triazine (tris-(dFB)Tz). The energy of the lowest unoccupied molecular orbital (E LUMO ) for tris-(dFB)Tz is estimated to be −3.5 eV from electrochemical measurements. The deep E LUMO of tris-(dFB)Tz affords a material with excellent electron acceptor characteristics for use in n-doped electron transport layers. Tris-(dFB)Tz shows a four order of magnitude increase in the number of carriers on doping with 8 wt. % Cs 2 CO 3 . Enhanced electron injection was also observed on doping with Cs 2 CO 3 , which eliminated the necessity for a separate LiF electron injection layer. Blue phosphorescent organic light-emitting devices (OLEDs) were fabricated using n-doped tris-(dFB)Tz electron transport layers. OLEDs with thick (700-Å) Cs 2 CO 3 -doped tris-(dFB)Tz electron transport layers had lower operating voltages than OLEDS with an undoped electron transport layer of bis(diphenylphosphoryl)dibenzothiophene (PO15), which has previously been used in lowvoltage, high-efficiency OLEDs. The tris-(dFB)Tz results indicate that aromatic substituted triazines may be promising materials for use as electron acceptors in n-doped organic electronic systems. C 2011 Society of Photo-Optical Instrumentation Engineers (SPIE).

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A triazine-based three-directional rigid-rod tecton forms a novel 1D channel structure

Abstract: A large, symmetrically substituted triazine-based molecule, synthesized by a copper-free Sonogashira coupling procedure self-assembles to form a novel 1D channel structure that hosts chlorobenzene molecules as guests.

Cited by 51 publications

References 37 publications

Star-Shaped Conjugated Systems

Star-Shaped Conjugated Systems

Oligomeric Tectonics: Supramolecular Assembly of Double‐Stranded Oligobisnorbornene through π–π Stacking

Blue phosphorescent organic light-emitting devices utilizing cesium–carbonate-doped 2,4,6-tris(2′,4′-difluoro-[1,1′-biphenyl]-4-yl)-1,3,5-triazine

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