Browse
Submit Data
Databases
API
Help

Dataset Information

2 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

2,7,11,16-Tetra-tert-Butyl Tetraindenopyrene Revisited by an "Inverse" Synthetic Approach.

ABSTRACT: A new synthetic route to tetraindenopyrene (TIP)-a bowl-shaped cut-out structure of C70 -is reported. The key step in this approach is a fourfold palladium-catalyzed C-H activation that increases the yield more than 50 times in comparison to the approach originally described by Scott and co-workers. Besides examination of its optoelectronic properties and study of its aggregation in solution, TIP was also re-investigated by dispersion-corrected DFT methods, which showed that dispersion interactions significantly increase the bowl-to-bowl inversion barrier. Furthermore, TIP was used as a semiconductor in p-channel thin-film transistors (TFTs).

SUBMITTER: Elbert SM

PROVIDER: S-EPMC7496754 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

2,7,11,16-Tetra-tert-Butyl Tetraindenopyrene Revisited by an "Inverse" Synthetic Approach.

Elbert Sven M SM Haidisch Anika A Kirschbaum Tobias T Rominger Frank F Zschieschang Ute U Klauk Hagen H Mastalerz Michael M

Chemistry (Weinheim an der Bergstrasse, Germany) 20200720 46

A new synthetic route to tetraindenopyrene (TIP)-a bowl-shaped cut-out structure of C<sub>70</sub> -is reported. The key step in this approach is a fourfold palladium-catalyzed C-H activation that increases the yield more than 50 times in comparison to the approach originally described by Scott and co-workers. Besides examination of its optoelectronic properties and study of its aggregation in solution, TIP was also re-investigated by dispersion-corrected DFT methods, which showed that dispersio ...[more]

PMID: 32314830

Similar Datasets

Tetra-kis(4-tert-butyl-benz-yl)silane.

Project description:The title compound, C(44)H(60)Si, was prepared as an inter-nal standard for diffusion-ordered NMR spectroscopy. The Si atom lies on a special position with site symmetry.

| S-EPMC3007930 | biostudies-literature

1,1,3,3-Tetra-tert-butyl-2,2-diisopropyl-4,4-diphenyl-cyclo-tetra-silane.

Project description:The molecule in the structure of the title compound, C34H60Si4, lies on a twofold rotation axis that passes through the two Si atoms, resulting in a planar cyclo-tetra-silane ring. The dihedral angle between the cyclo-tetra-silane ring and the phenyl ring is 68.20?(5)°. The Si-Si bonds [2.4404?(8) and 2.4576?(8)?Å] are longer than a standard Si-Si bond (2.34?Å) and the C-Si-C bond angle [97.07?(14)°] of the phenyl-substituted Si atom is smaller than the tetra-hedral bond angle (109.5°). These long bonds and small bond angle are favorable for reducing the steric hindrance among the bulky substituents.

| S-EPMC3588281 | biostudies-literature

5,11,17,23-Tetra-tert-butyl-25,26,27,28-tetra-propyn-yloxy-2,8,14,20-tetra-thia-calix[4]arene.

Project description:THE TITLE COMPOUND [SYSTEMATIC NAME: 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetra-propyn-yloxy-2,8,14,20-tetra-thia-calix[4]arene], C(52)H(56)O(4)S(4), is an alkyl-ated product bearing four propyne groups at the lower rim of a 5,11,17,23-tetra-tert-butyl-tetrathia-calix[4]arene. The mol-ecule is located on a crystallographic twofold rotation axis, running through two S atoms and perpendicular to the long axis of the mol-ecule. The four propyne groups, located in an alternate fashion above and below the mean plane of the four S atoms, are almost parallel to the calixarene long axis. The dihedral angle between the two crystallographically independent benzene rings is 86.77?(14)°. Two tert-butyl groups are disordered over two positions with site occupancies of 0.59?(2) and 0.41?(2).

| S-EPMC2972022 | biostudies-literature

25,26,27,28-Tetra-butoxy-5,11,17,23-tetra-tert-butyl-calix[4]arene chloro-form tetra-solvate dihydrate.

Project description:The title compound, C(60)H(88)O(4)·4CHCl(3)·2H(2)O, is the alkyl-ated product of 5,11,17,23-tetra-tert-butyl-calix[4]arene. It adopts a distorted cone conformation which leads to an open cavity. All the phenolic rings are tilted so that their tert-butyl groups are pitched away from the calix cavity. Two opposite aromatic rings are close to being perpendicular to one another [dihedral angle 85.0?(2)°], while the other pair of opposite rings is almost parallel [dihedral angle 8.1?(2)°], and adjacent phenolic rings are almost perpendicular [dihedral angles 82.4?(1) or 87.9?(1)°]. In the crystal, the water molecule and calixarene interact by way of O-H?O hydrogen bonds.

| S-EPMC2969488 | biostudies-literature

3,9-Di-tert-butyl-2,4,8,10-tetra-oxaspiro-[5.5]undeca-ne.

Project description:The title compound, C(15)H(28)O(4), was prepared by the condensation of pivalaldehyde with penta-erythritol. In the crystal, the two halves of the mol-ecule are related by a crystallographic twofold rotation axis passing through the central spiro-C atom. The two non-planar six-membered heterocycles both adopt chair conformations with the two tert-butyl groups both located in the equatorial positions.

| S-EPMC3011739 | biostudies-literature

tert-Butyl-ammonium 2,3,4,5-tetra-chloro-6-methoxy-carbonyl-benzoate.

Project description:In the title compound, C(4)H(12)N(+)·C(9)H(3)Cl(4)O(4) (-), the benzene ring forms dihedral angles of 62.4 (2) and 64.0 (3)°, respectively, with the essentially planar methoxy-carbonyl and carboxyl-ate groups. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds connect anions and cations, forming one-dimensional chains along [010].

| S-EPMC2959952 | biostudies-literature

1,1,4,4-Tetra-tert-butyl-1,4-dichloro-2,2,3,3-tetra-phenyl-tetra-silane.

Project description:The title compound, C(40)H(56)Cl(2)Si(4), was synthesized by the coupling of 1,1-di-tert-butyl-1,2-dichloro-2,2-diphenyl-disilane with lithium. The asymmetric unit contains one half-mol-ecule, which is completed by an inversion centre. In the mol-ecule, the tetra-silane skeleton adopts a perfect anti conformation and the Si-Si bonds [2.4355?(5) and 2.4328?(7)?Å] are longer than the standard Si-Si bond length (2.34?Å). The Si-Si-Si angle [116.09?(2)°] is larger than the tetra-hedral bond angle (109.5°). These long bond lengths and the wide angle are favorable for reducing the steric hindrance among the tert-butyl and the phenyl groups. The dihedral angle between the phenyl rings in the asymmetric unit is 37.36?(8)°.

| S-EPMC3275182 | biostudies-other

Crystal structure of tert-butyl-N-phenyl-carbonitrilium tetra-chlorido-aluminate.

Project description:In the title compound, (C11H14N)[AlCl4], the nitrilium (systematic name: 2,2-dimethyl-N-phenyl-propane-nitrilium) ion adopts a slightly distorted linear configuration [C-N C = 178.87?(16) and N C-C = 179.13?(17)°]. In the crystal, while there are no inter-molecular hydrogen bonds, pairs of nitrilium ions are linked through ?-? inter-actions [inter-centroid distance = 3.8091?(13)?Å].

| S-EPMC4257323 | biostudies-literature

Tetra-kis(?-4-tert-butyl-benzoato)-?O:O';?O,O':O';?O:O,O'-bis-[aqua-(4-tert-butyl-benzoato-?O,O')(4-tert-butyl-benzoic acid-?O)neodymium(III)].

Project description:The reaction of neodymium nitrate and 4-tert-butyl-benzoic acid (tBBAH) in aqueous solution yielded the dinuclear title complex, [Nd(2)(C(11)H(13)O(2))(6)(C(11)H(14)O(2))(2)(H(2)O)(2)], which has non-crystallographic C(i) symmetry. The two Nd(III) ions are linked by two bridging and two bridging-chelating tBBA ligands with an Nd?Nd separation of 4.0624?(5)?Å. Moreover, each Nd(III) ion is coordinated by one chelating tBBA ion, one monodentate tBBAH ligand and one water mol-ecule. The nine-coordinated Nd(III) ion is in a distorted tricapped trigonal-prismatic environment. The mol-ecules are linked into infinite chains along the c axis by inter-molecular O-H?O hydrogen bonds. Three of the tert-butyl groups are disordered over two sets of sites with equal occupancies.

| S-EPMC3120497 | biostudies-literature

2-(4-Bromo-benz-yl)-5,11,17,23-tetra-tert-butyl-25,26,27,28-tetra-methoxy-calix[4]arene.

Project description:In the title compound, C(55)H(69)BrO(4), the calixarene mol-ecule displays a 'partial cone' conformation bearing the lateral substituent in a sterically favorable equatorial arrangement between two syn-orientated arene units. The crystal packing is stabilized by weak C-H?? contacts, involving one tert-butyl group, and ?-stacking inter-actions of the lateral bromo-benzene units [centroid-centroid distance = 3.706?(1)?Å].

| S-EPMC2969344 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data