Supramolecular Chirality: Chiral hydrogen-bonded supermolecules from achiral molecular components

1998 ◽  
Vol 81 (1) ◽  
pp. 1-13 ◽  
Author(s):  
Mauricio Suárez ◽  
Neil Branda ◽  
Jean-Marie Lehn ◽  
André Decian ◽  
Jean Fischer
Keyword(s):  
Supramolecular Chirality ◽  
Molecular Components ◽  
Hydrogen Bonded

Hydrogen-bonded supercoil self-assembly from achiral molecular components with light-driven supramolecular chirality

2014 ◽  
Vol 2 (31) ◽  
pp. 6402-6409 ◽  
Author(s):  
Yangyang Wang ◽  
Deyan Zhou ◽  
Haining Li ◽  
Ruiru Li ◽  
Yueyao Zhong ◽  
...  
Keyword(s):  
Self Assembly ◽  
Molecular Hydrogen ◽  
Supramolecular Chirality ◽  
Self Assembled ◽  
Molecular Components ◽  
Hydrogen Bonded

Supercoils self-assembled from two achiral molecular hydrogen-bonded components have been studied for in-depth understanding of the structure and functionality of this chiral supramolecular association.

Light-Driven Supramolecular Chirality in Propeller-Like Hydrogen-Bonded Complexes That Show Columnar Mesomorphism

2007 ◽  
Vol 119 (11) ◽  
pp. 1905-1909 ◽  
Author(s):  
Francisco Vera ◽  
Rosa M. Tejedor ◽  
Pilar Romero ◽  
Joaquín Barberá ◽  
M. Blanca Ros ◽  
...  
Keyword(s):  
Supramolecular Chirality ◽  
Bonded Complexes ◽  
Hydrogen Bonded

scholarly journals (2E)-3-(6-Methoxynaphthalen-2-yl)-1-(pyridin-3-yl)prop-2-en-1-one and its cyclocondensation product with guanidine, (4RS)-2-amino-4-(6-methoxynaphthalen-2-yl)-6-(pyridin-3-yl)-3,4-dihydropyrimidine monohydrate: two types of hydrogen-bonded sheet

2014 ◽  
Vol 70 (11) ◽  
pp. 1011-1016 ◽  
Author(s):  
Prakash S. Nayak ◽  
Badiadka Narayana ◽  
Hemmige S. Yathirajan ◽  
Eric C. Hosten ◽  
Richard Betz ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Dihedral Angles ◽  
Form Complex ◽  
Molecular Components ◽  
Hydrogen Bonded

The structures of a chalcone and of its cyclocondensation product with guanidine are reported. In (2E)-3-(6-methoxynaphthalen-2-yl)-1-(pyridin-3-yl)prop-2-en-1-one, C19H15NO2, (I), the planes of the pyridine and naphthalene units make dihedral angles with that of the central spacer unit of 23.61 (13) and 23.57 (15)°, respectively, and a dihedral angle of 47.24 (9)° with each other. The molecules of (I) are linked into sheets by a combination of C—H...O and C—H...π(arene) hydrogen bonds. In the cyclocondensation product (4RS)-2-amino-4-(6-methoxynaphthalen-2-yl)-6-(pyridin-3-yl)-3,4-dihydropyrimidine monohydrate, C20H18N4O·H2O, (II), the dihydropyrimidine ring adopts a conformation best described as a shallow boat. The molecular components are linked by two N—H...O hydrogen bonds, two O—H...N hydrogen bonds and one N—H...N hydrogen bond to form complex sheets, with the methoxynaphthalene interdigitated between inversion-related pairs of sheets.

Chiral versus racemic building blocks in supramolecular chemistry: malate salts of organic diamines

2002 ◽  
Vol 58 (3) ◽  
pp. 530-544 ◽  
Author(s):  
Dorcas M. M. Farrell ◽  
George Ferguson ◽  
Alan J. Lough ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonds ◽  
Supramolecular Chemistry ◽  
Malic Acid ◽  
Three Dimensional ◽  
Building Blocks ◽  
Partial Transfer ◽  
Molecular Components ◽  
N Vector ◽  
Hydrogen Bonded

(S)-Malic acid forms a salt with N,N′-dimethylpiperazine, [MeN(CH2CH2)2NMe]H2 2+·2C4H5O5 − (1) (triclinic, P1, Z′ = 1), in which the cations link pairs of hydrogen-bonded anion chains to form a molecular ladder. With 4,4′-bipyridyl, (S)-malic acid forms a 1:1 adduct which crystallizes from methanol to yield two polymorphs, (2) (triclinic, P1, Z′ = 1) and (3) (monoclinic, C2, Z′ = 1), while racemic malic acid with 4,4′-bipyridyl also forms a 1:1 adduct, (4) (monoclinic, P21/c, Z′ = 1). In each of (2), (3) and (4) the components are linked by O—H...N and N—H...O into chains of alternating bipyridyl and malate units, which are linked into sheets by O—H...O hydrogen bonds. In each of the 1:1 adducts (5) and (6), formed by, respectively, (S)-malic acid and racemic malic acid with 1,2-bis(4′-pyridyl)ethene, the diamine is disordered over two sets of sites, related by a 180° rotation about the N...N vector. In (5), (C12H10N2)H+·C4H5O5 − (triclinic, P1, Z′ = 1), the components are again linked by a combination of N—H...O and O—H...O hydrogen bonds into sheets, while in (6) (triclinic, P{\overline 1}, Z′ = 0.5) there is only partial transfer of the H atom from O to N and the malate component is disordered across a centre of inversion. With 1,4-diazabicyclo[2.2.2]octane, racemic malic acid forms a 1:2 salt, [(C6H12N2)H2]2+·2C4H5O5 − (7) (monoclinic, P21/c, Z′ = 2), while (S)-malic acid forms a 1:1 adduct, (8) (monoclinic, P21, Z′ = 3). There are thus six independent molecular components in each. In (7) the ions are linked by an extensive series of N—H...O and O—H...O hydrogen bonds into a three-dimensional framework, but in (8) there is extensive disorder involving all six components, and no refinement proved to be feasible.

Chiral triptycene-pyrene π-conjugated chromophores with circularly polarized luminescence

2017 ◽  
Vol 15 (39) ◽  
pp. 8440-8447 ◽  
Author(s):  
Tomoyuki Ikai ◽  
Yuya Wada ◽  
Seiya Awata ◽  
Changsik Yun ◽  
Katsuhiro Maeda ◽  
...  
Keyword(s):  
Circularly Polarized ◽  
Supramolecular Chirality ◽  
Circularly Polarized Luminescence ◽  
Polarized Luminescence ◽  
Hydrogen Bonded

Novel chiral triptycenes showing circularly polarized luminescence based on the supramolecular chirality induced in the hydrogen-bonded aggregate have been developed.

Complete asymmetric induction of supramolecular chirality in a hydrogen-bonded assembly

Nature ◽  
10.1038/19053 ◽  
1999 ◽  
Vol 398 (6727) ◽  
pp. 498-502 ◽  
Author(s):  
Leonard J. Prins ◽  
Jurriaan Huskens ◽  
Feike de Jong ◽  
Peter Timmerman ◽  
David N. Reinhoudt
Keyword(s):  
Asymmetric Induction ◽  
Supramolecular Chirality ◽  
Hydrogen Bonded

(Z)-5-[(5-Methyl-1H-imidazol-4-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one monohydrate: a three-dimensional hydrogen-bonded framework structure

2012 ◽  
Vol 68 (11) ◽  
pp. o468-o471 ◽  
Author(s):  
Alberto Insuasty ◽  
Braulio Insuasty ◽  
Justo Cobo ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Title Compound ◽  
Three Dimensional ◽  
Organic Component ◽  
Framework Structure ◽  
Compound C ◽  
Molecular Components ◽  
Hydrogen Bonded

The non-H atoms in the organic component of the title compound, C8H7N3OS2·H2O, are almost coplanar, as the dihedral angle between the two ring planes is only 1.8 (2)°; there is a wide C—C—C angle of 127.8 (3)° at the methine C atom linking the two rings. The molecular components are linked into a three-dimensional framework structure by two-centre hydrogen bonds of N—H...O and O—H...N types, together with a three-centre O—H...(N,S) system. Comparisons are made with some (Z)-5-arylmethylidene-2-sulfanylidene-1,3-thiazolidin-4-ones.

Supramolecular Chirality of Hydrogen-Bonded Rosette Assemblies

ChemInform ◽  
2007 ◽  
Vol 38 (30) ◽  
Author(s):  
Socorro Vazquez-Campos ◽  
Mercedes Crego-Calama ◽  
David N. Reinhoudt
Keyword(s):  
Supramolecular Chirality ◽  
Hydrogen Bonded
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