Nanoribbons or Weakly Connected Acenes? The Influence of Pyrene Insertion on Linearly Extended Ring Systems

2021 ◽  
Author(s):  
Qianxiang Ai ◽  
Tanner Smith ◽  
A.D. Thilanga Liyanage ◽  
Samuel Mazza ◽  
Sean R. Parkin ◽  
...  
Keyword(s):  
Chemical Stability ◽  
System Size ◽  
Conjugated Molecules ◽  
Ring Systems ◽  
Benzene Rings ◽  
Lateral Fusion

Derived from the lateral fusion of benzene rings, acenes are a class of π-conjugated molecules containing a single aromatic sextet, where system size is inversely correlated with chemical stability. In...

scholarly journals (1-Adamantyl){4-[(2-chloro-9-isopropyl-9H-purin-6-yl)aminomethyl]phenyl}methanone trichloromethane solvate

2009 ◽  
Vol 65 (6) ◽  
pp. o1268-o1268 ◽  
Author(s):  
Michal Rouchal ◽  
Marek Nečas ◽  
Robert Vícha
Keyword(s):  
Interplanar Distance ◽  
Maximum Deviation ◽  
Stacking Interactions ◽  
Ring Systems ◽  
Face To Face ◽  
Compound C ◽  
Centroid Distance ◽  
Benzene Rings ◽  
Purine Ring ◽  
Centrosymmetric Dimers

In the title compound, C26H30ClN5O·CHCl3, the purine molecule consists of essentially planar benzene and purine ring systems [maximum deviation 0.010 (4) Å for both ring systems] forming a dihedral angle of 85.52 (9)°. Intermolecular N—H...N hydrogen bonds link adjacent molecules into centrosymmetric dimers. The structure also contains intermolecular C—H...O and C—H...N interactions. The benzene rings form offset face-to-face π–π stacking interactions with an interplanar distance of 3.541 (4) Å and a centroid-to-centroid distance of 4.022 (4) Å.

scholarly journals Crystal structures of three indole derivatives: 3-ethnyl-2-methyl-1-phenylsulfonyl-1H-indole, 4-phenylsulfonyl-3H,4H-cyclopenta[b]indol-1(2H)-one and 1-{2-[(E)-2-(5-chloro-2-nitrophenyl)ethenyl]-1-phenylsulfonyl-1H-indol-3-yl}ethan-1-one chloroform monosolvate

2015 ◽  
Vol 71 (9) ◽  
pp. 1036-1041
Author(s):  
S. Gopinath ◽  
K. Sethusankar ◽  
Bose Muthu Ramalingam ◽  
Arasambattu K. Mohanakrishnan
Keyword(s):  
Molecular Structure ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Dihedral Angles ◽  
Indole Derivatives ◽  
Indole Ring ◽  
Asymmetric Unit ◽  
Ring Systems ◽  
Benzene Rings ◽  
Independent Molecules

The title compounds, C17H13NO2S, (I), C17H13NO3S, (II), and C24H17ClN2O5S·CHCl3, (III), are indole derivatives. Compounds (I) and (II) crystalize with two independent molecules in the asymmetric unit. The indole ring systems in all three structures deviate only slightly from planarity, with dihedral angles between the planes of the pyrrole and benzene rings spanning the tight range 0.20 (9)–1.65 (9)°. These indole ring systems, in turn, are almost orthogonal to the phenylsulfonyl rings [range of dihedral angles between mean planes = 77.21 (8)–89.26 (8)°]. In the three compounds, the molecular structure is stabilized by intramolecular C—H...O hydrogen bonds, generatingS(6) ring motifs with the sulfone O atom. In compounds (I) and (II), the two independent molecules are linked by C—H...O hydrogen bonds and C—H...π interactions, while in compound (III), the molecules are linked by C—H...O hydrogen bonds, generatingR22(22) inversion dimers.

scholarly journals 4-(Benzo[d]thiazol-2-yl)-N,N-dimethylaniline

IUCrData ◽  
2016 ◽  
Vol 1 (11) ◽  
Author(s):  
Yi-Wen Tang ◽  
Jing-Hang Wang ◽  
Qing-Yuan Xie ◽  
Quan Wang ◽  
Jie-Ying Wu
Keyword(s):  
Title Compound ◽  
Stacking Interactions ◽  
Ring Systems ◽  
Compound C ◽  
Π Stacking ◽  
Benzene Rings ◽  
Best Fit

The whole molecule of the title compound, C15H14N2S, is approximately planar, with an r.m.s. deviation of 0.0382 Å from the best-fit mean plane through all 18 non-H atoms. In the crystal, dimers form through π–π stacking interactions between the benzene rings of adjacent benzothiazole ring systems, with a centroid–centroid separation of 3.6834 (16) Å.

scholarly journals 6-(1-Adamantyl)-3-(2-fluorophenyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole

2009 ◽  
Vol 65 (6) ◽  
pp. o1437-o1437 ◽  
Author(s):  
Mahmood-ul-Hassan Khan ◽  
Shahid Hameed ◽  
M. Nawaz Tahir ◽  
Tanveer Hussain Bokhari ◽  
Islam Ullah Khan
Keyword(s):  
Dihedral Angle ◽  
Title Compound ◽  
Ring Systems ◽  
Π Interactions ◽  
Compound C ◽  
Benzene Rings ◽  
Thiadiazole Ring

In the title compound, C19H19FN4S, the planes of the 2-fluorophenyl and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole ring systems are oriented at a dihedral angle of 48.98 (6)°. In the crystal, weak C—H...S and C—H...π interactions may help to establish the packing and π–π interactions between the centroids of the benzene rings at a distance of 3.8792 (13) Å occur.

scholarly journals (Z)-N′-(3-Ethyl-4-oxothiazolidin-2-ylidene)-2-[6-(4-methoxyphenyl)imidazo[2,1-b]thiazol-3-yl]acetohydrazide

IUCrData ◽  
2017 ◽  
Vol 2 (1) ◽  
Author(s):  
Zeliha Atioğlu ◽  
Mehmet Akkurt ◽  
Faika Başoğlu ◽  
Nuray Ulusoy Güzeldemirci ◽  
Rahmi Köseoğlu ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Thiazole Ring ◽  
Dihedral Angles ◽  
Asymmetric Unit ◽  
Triclinic Space Group ◽  
Ring Systems ◽  
Compound C ◽  
Benzene Rings ◽  
The Mean ◽  
Independent Molecules

The title compound, C19H19N5O3S2, crystallizes in the triclinic space groupP-1, with two independent molecules (AandB) in the asymmetric unit (Z′ = 2). The imidazo[2,1-b][1,3]thiazole ring systems in moleculesAandBare essentially planar (r.m.s deviations = 0.004 and 0.005 Å, respectively), with dihedral angles of 1.1 (3) and 0.8 (3)°, respectively, between the thiazole and imidazole rings. The mean planes of these ring systems make dihedral angles of 16.0 (2) and 61.9 (2)° for moleculeA, and 11.8 (2) and 74.3 (2)° for moleculeB, with the 1,3-thiazolidine and methoxy-substituted benzene rings, respectively. In the crystal, molecules are linkedviaN—H...O hydrogen bonds, forming –A–B–A–B– chains along [100]. The chains are linked by C—H...O hydrogen bonds, forming layers parallel to theabplane.

scholarly journals Affirmative polymorph generation of annulenes by using CH/O interactions

2014 ◽  
Vol 70 (a1) ◽  
pp. C543-C543
Author(s):  
Ichiro Hisaki ◽  
Norimitsu Tohnai ◽  
Mikiji Miyata
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Methyl Ester ◽  
Ester Group ◽  
Strong Hydrogen Bond ◽  
Weak Hydrogen Bond ◽  
Conjugated Molecules ◽  
Pi Conjugated ◽  
Polymorphic Crystals ◽  
Benzene Rings

CH/O interaction is recognized as a weak hydrogen bond with less directionality, compared with a strong hydrogen bond such as that between carboxylic acids. Therefore, the interaction does not seem to be suitable for precise design of crystal structures. In connection with this, however, we emphasized that the CH/O interaction, particularly that provided by methyl ester group, can utilize for affirmative generation of polymorphs of cyclic pi conjugated molecules. Since functionality of solid state materials based on pi conjugated molecules is crucially affected by their molecular arrangements, polymorphs are exactly appropriate systems to reveal the superstructure-dependent properties of such the materials, and therefore, affirmative preparation of polymorphs of pi conjugated molecules is challenging. Herein, we describe formation, crystallographic characterization, and superstructure-dependent properties of polymorphs of methyl ester functionalized dehydrobenzoannulenes (DBAs), a family of cyclic conjugated molecules consisted of benzene rings and acetylene units. We synthesized five DBA derivatives 1-5 with two types of annulene cores (octadehydrodibenzo[12]annulene and octadehydrotribenzo[14]annulene cores) and different number and position of methyl ester groups (Scheme1). These derivatives exhibit two to five polymorphic crystals with physical properties strongly depending with their supramolecular structures.[1-3] We believe that the present polymorph generation is exactly provided by rotationally flexible conformations of the ester groups and versatile ways of directionally tolerant CH/O interactions of the ester groups.

scholarly journals 1-{[(2,3-Dihydro-1H-inden-2-yl)oxy]methyl}quinazoline-2,4(1H,3H)-dione

2012 ◽  
Vol 68 (6) ◽  
pp. o1866-o1867 ◽  
Author(s):  
Nasser R. El-Brollosy ◽  
Necmi Dege ◽  
Güneş Demirtaş ◽  
Mohamed I. Attia ◽  
Ali A. El-Emam ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Membered Ring ◽  
Ring Systems ◽  
Π Interactions ◽  
Envelope Conformation ◽  
Centroid Distance ◽  
Benzene Rings ◽  
The Mean ◽  
Title Molecule

In the title molecule, C18H16N2O3, the five-membered ring has an envelope conformation, with the substituted C atom deviating by 0.342 (4) Å from the mean plane P calculated for the remainder of the non-H atoms of the 2,3-dihydro-1H-indene fragment. The mean planes of quinazoline-2,4(1H,3H)-dione fragment and P form a dihedral angle of 59.08 (4)°. In the crystal, pairs of N—H...O hydrogen bonds link molecules into inversion dimers, and weak C—H...O hydrogen bonds and π–π interactions between the benzene rings of the quinazoline ring systems [centroid–centroid distance = 3.538 (3) Å] further consolidate the packing.

scholarly journals Crystal structure of 4′-bromo-2,5-dihydroxy-2′,5′-dimethoxy-[1,1′-biphenyl]-3,4-dicarbonitrile

2016 ◽  
Vol 72 (5) ◽  
pp. 667-670 ◽  
Author(s):  
Joseph E. Meany ◽  
Steven P. Kelley ◽  
Robin D. Rogers ◽  
Stephen A. Woski
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Dimensional Structure ◽  
Two Dimensional ◽  
Ring Systems ◽  
Bond Forming ◽  
Benzene Rings

In the crystal of the title substituted hemibiquinone derivative, C16H11BrN2O4or [BrHBQH2(CN)2], the substituted benzene rings are rotated about the central C—C bond, forming a dihedral angle of 53.59 (7)°. The ring systems interact through an intramolecular O—H...Omethoxyhydrogen bond, which induces a geometry quite different from those in previously reported hemibiquinone structures. In the crystal, the molecules associate through an intermolecular O—H...Nnitrilehydrogen bond, forming chains which extend along [100] and are interlinked through very weak C—H...N hydrogen bonds, giving a overall two-dimensional structure lying parallel to (010).

scholarly journals Crystal structure of (2E,3E)-N2,N3-bis(3-ethyl-[1,1′-biphenyl]-4-yl)butane-2,3-diimine

2015 ◽  
Vol 71 (4) ◽  
pp. o251-o252 ◽  
Author(s):  
Yan Zhao ◽  
Jianchao Yuan ◽  
Jie Zhao ◽  
Shenglan Zhao
Keyword(s):  
Crystal Structure ◽  
Title Compound ◽  
Condensation Reaction ◽  
Maximum Deviation ◽  
Ring Systems ◽  
Π Interactions ◽  
Compound C ◽  
Benzene Rings ◽  
The Mean

In the title compound, C32H32N2, synthesized by the condensation reaction of 2-ethyl-4-phenylaniline and 2,3-butanedione, the conformation about the C=N bonds isEand the substituted biphenyl units aretransto one another. In the two biphenyl ring systems, the planes of the two rings are inclined to one another by 25.25 (19) and 28.01 (19)°. The planes of the ethyl-substituted benzene rings are inclined to one another by 20.23 (19)° and to the mean plane of the butane-2,3-diimine unit [maximum deviation = 0.014 (4) Å] by 83.19 (19) and 63.38 (19)°. In the crystal, molecules are linked by C—H...π interactions, forming sheets lying parallel to (101).

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