Search results for "Annulene"

Complexation and Electronic Communication between Corannulene-Based Buckybowls and a Curved Truxene-TTF Donor

2017

Abstract: The association behavior of an electron-donating, bowl-shaped, truxene-based tetrathiafulvalene (truxTTF) with two corannulene-based fullerene fragments, C32H12 and C38H14, is investigated in several solvents. Formation of 1:1 complexes is followed by absorption titrations and complemented by density functional theory (DFT) calculations. The binding constants are in the range logKa=2.9–3.5. DFT calculations reveal that the most stable arrangement is the conformation in which the 1,3-dithiole ring of truxTTF is placed inside the concave cavity of the corannulene derivative. This arrangement is confirmed experimentally by NMR measurements, and implies that a combination of p–p and C…

syn-1,6-imino-8,13-oxido[14]annulene

1990

Abstract syn -1,6-Imino-8,13-oxido[14]annulene (1) , an aromatic annulene featuring closely spaced NH and O-bridges, has been synthesized. Contrary to expectation, NH ⋯ O hydrogen bonding in I does not profit from the proximity of the functionalities noticeably.

Aggregation and Photodimerization of Areno-Condensed Annulenes

2001

Triphenanthro‐anellierte [18]Annulene mit Alkoxy‐Seitenketten — Eine neue Klasse discotischer Flüssigkristalle

1994

Triphenanthro-Anellated [18]Annulenes with Alkoxy Side Chains - A Novel Class of Discotic Liquid Crystals Two different types 6 and 16 of [18]annulenes condensed with phenanthrene systems were prepared by cyclocondensation reactions (Schemes 2 and 3). The central 18-membered rings do not show a macrocyclic diamagnetic ring current. Conformational analyses and X-ray analyses in the solid state reveal non-planar structures in which aromatic “islands” are connected by (E)-configurated olefinic bridges. The introduction of long alkoxy side chains yields a new class of discotic liquid crystals; either ND or hexagonal columnar phases are generated, which were characterized by DSC, microscopy with…

1,2,3,4,5‐[1′,8′] Anthra‐8,9;10,11‐dibenzo[13]annulene and 1,8‐Distyrylanthracene as Models for Phenylenevinylene Species. Syntheses, Structures, and…

1987

The synthesis of the title compound 4, formally a [13] perimeter, and of its acyclic model system, 1,8-distyrylanthracene (6) is described. The crystal structure of 4 reveals the configuration of the double bonds and the conformation of the macrocycle. Related findings come from the 1H-NMR spectroscopic characterization of 4 and 6 in solution. The spin density distribution of the radical anions 4−· and 6−· is interpretet in terms of the singly occupied molecular orbital and of the prevailing geometry. In contrast to 4, compund 6 proves to be an efficient electron acceptor since it can even be reduced to a tetraanion salt. The complete redox sequence is characterized by NMR and ESR spectrosc…

Corrigendum: An Unusually Small Singlet-Triplet Gap in a Quinoidal 1,6-Methano[10]annulene Resulting from Baird's 4n π-Electron Triplet Stabilization.

2016

Within the continuum of π-extended quinoidal electronic structures exist molecules that by design can support open-shell diradical structures. The prevailing molecular design criteria for such structures involve proaromatic nature that evolves aromaticity in open-shell diradical resonance structures. A new diradical species built upon a quinoidal methano[10]annulene unit is synthesized and spectroscopically evaluated. The requisite intersystem crossing in the open-shell structure is accompanied by structural reorganization from a contorted Mobius aromatic-like shape in S0 to a more planar shape in the Huckel aromatic-like T1. This stability was attributed to Baird’s Rule which dictates the …

Photoreactive Liquid Crystals in the Series of Dendritic and Cyclic Stilbenoid Compounds

2000

The dendrimers 1 and 2 and the areno-condensed annulenes 3 and 4 represent new mesogens for the generation of discotic mesophases. The stilbenoid building blocks of these compounds provide the molecular basis for interesting photochemical and photophysical effects like dimerisation, oligomerisation or the formation of charge carriers.

A new synthetic route to tribenzo[a,e,i][12]annulenes

2000

Abstract The tribenzo[a,e,i][12]annulene 10 and the corresponding twofold annulene 14 were prepared on synthetic routes which first led from suitably functionalised starting compounds (2, 11) to the 1,2-distyryl- and 1,2,3,4-tetrastyrylbenzene derivatives 9 and 13 with two and four formyl groups, respectively. The cyclisation to 10 and 14 was achieved by applying the McMurry reaction. The extended ring system of compound 14 represents a discotic mesogen. The generation of liquid crystals was obtained with eight hexyloxy chains on the periphery.

ChemInform Abstract: A New Synthetic Route to Tribenzo[a,e,i][12]annulenes.

2010

Abstract The tribenzo[a,e,i][12]annulene 10 and the corresponding twofold annulene 14 were prepared on synthetic routes which first led from suitably functionalised starting compounds (2, 11) to the 1,2-distyryl- and 1,2,3,4-tetrastyrylbenzene derivatives 9 and 13 with two and four formyl groups, respectively. The cyclisation to 10 and 14 was achieved by applying the McMurry reaction. The extended ring system of compound 14 represents a discotic mesogen. The generation of liquid crystals was obtained with eight hexyloxy chains on the periphery.

Torsional Bias as a Strategy To Tune Singlet–Triplet Gaps in Organic Diradicals

2018

Quinoidal compounds with proaromatic structures possess differing degrees of diradical character, where the open-shell diradical resonance form has restored aromaticity throughout the compound. Methods to tune the diradical character of these compounds have traditionally focused on altering the length and the molecular composition of the π-conjugated backbones. However, other molecular design strategies to tune the singlet–triplet gap of π-conjugated quinoidal molecules have not been extensively explored. We previously reported a strikingly small energy gap between the quinoidal and diradical states of a quinoidal small molecule containing methano[10]annulene (TMTQ) that was dictated in lar…