Browse
Submit Data
Databases
API
Help

Dataset Information

11 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

The efficient synthesis of dibenzo[d,d']benzo[1,2-b:4,3-b']dithiophene and cyclopenta[1,2-b:4,3-b']bis(benzo[d]thiophen)-6-one.

ABSTRACT: With 3,3'-bi[benzo[b]thiophenyl] as starting material, dibenzo[d,d']benzo[1,2-b:4,3-b']dithiophene, a [5]heterohelicene, was synthesized efficiently in 60% yield via formylation and McMurry reaction. Cyclopenta[1,2-b:4,3-b']bis(benzo[d]thiophen)-6-one, another interesting helical ketone, was also prepared in 79% yield via deprotonation and ketonization of 3,3'-bi[benzo[b]thiophenyl]. In addition, the single-crystal structure of dibenzo[d,d']benzo[1,2-b:4,3-b']dithiophene and UV-vis spectra of both title compounds are described.

SUBMITTER: Wang Z

PROVIDER: S-EPMC2814327 | biostudies-literature | 2009 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

The efficient synthesis of dibenzo[d,d']benzo[1,2-b:4,3-b']dithiophene and cyclopenta[1,2-b:4,3-b']bis(benzo[d]thiophen)-6-one.

Wang Zhihua Z Zhu Sheng S Shi Jianwu J Wang Hua H

Beilstein journal of organic chemistry 20091013

With 3,3'-bi[benzo[b]thiophenyl] as starting material, dibenzo[d,d']benzo[1,2-b:4,3-b']dithiophene, a [5]heterohelicene, was synthesized efficiently in 60% yield via formylation and McMurry reaction. Cyclopenta[1,2-b:4,3-b']bis(benzo[d]thiophen)-6-one, another interesting helical ketone, was also prepared in 79% yield via deprotonation and ketonization of 3,3'-bi[benzo[b]thiophenyl]. In addition, the single-crystal structure of dibenzo[d,d']benzo[1,2-b:4,3-b']dithiophene and UV-vis spectra of bo ...[more]

PMID: 20126557

Similar Datasets

N,N'-Bis[1-(thiophen-2-yl)ethylidene]ethane-1,2-diamine.

Project description:Mol-ecules of the title compound, C(14)H(16)N(2)S(2), have a centre of inversion in the middle of the -CH(2)-CH(2)- bond; the (C(4)H(3)S)(CH(3))C=N-CH(2)- moiety is almost planar (r.m.s. deviation for non-H atoms 0.027?Å).

| S-EPMC3200618 | biostudies-literature

1,2-Bis(4-nitro-benzo-yl)hydrazine.

Project description:The title mol-ecule, C(14)H(10)N(4)O(6), crystallizes with one half-mol-ecule in the asymmetric unit; the mid-point of the N-N bond lies on an inversion centre. The nitro and amide groups are twisted with respect to the benzene ring, making dihedral angles of 14.6?(5) and 31.1?(5)°, respectively. In the crystal structure, mol-ecules are linked through N-H?O hydrogen bonding between the imino and carbonyl groups.

| S-EPMC2970062 | biostudies-literature

Chlorinated Benzo[1,2-b:4,5-c']dithiophene-4,8-dione Polymer Donor: A Small Atom Makes a Big Difference.

Project description:The position of a chlorine atom in a charge carrier of polymer solar cells (PSCs) is important to boost their photovoltaic performance. Herein, two chlorinated D-A conjugated polymers PBBD-Cl-? and PBBD-Cl-? are synthesized based on two new building blocks (TTO-Cl-? and TTO-Cl-?) respectively by introducing the chlorine atom into ? or ? position of the upper thiophene of the highly electron-deficient benzo[1,2-b:4,5-c']dithiophene-4,8-dione moiety. Single-crystal analysis demonstrates that the chlorine-free TTO shows a ?-? stacking distance (d ?-?) of 3.55 Å. When H atom at the ? position of thiophene of TTO is replaced by Cl, both ?-? stacking distance (d ?-? = 3.48 Å) and Cl···S distance (d Cl-S = 4.4 Å) are simultaneously reduced for TTO-Cl-? compared with TTO. TTO-Cl-? then showed the Cl···S non-covalent interaction can further shorten the intermolecular ?-? stacking separation to 3.23 Å, much smaller than that of TTO-Cl-? and TTO. After blending with BTP-eC9, PBBD-Cl-?:BTP-eC9-based PSCs achieved an outstanding power conversion efficiency (PCE) of 16.20%, much higher than PBBD:BTP-eC9 (10.06%) and PBBD-Cl-?:BTP-eC9 (13.35%) based devices. These results provide an effective strategy for design and synthesis of highly efficient donor polymers by precise positioning of the chlorine substitution.

| S-EPMC7887605 | biostudies-literature

Side-chain Engineering of Benzo[1,2-b:4,5-b']dithiophene Core-structured Small Molecules for High-Performance Organic Solar Cells.

Project description:Three novel small molecules have been developed by side-chain engineering on benzo[1,2-b:4,5-b']dithiophene (BDT) core. The typical acceptor-donor-acceptor (A-D-A) structure is adopted with 4,8-functionalized BDT moieties as core, dioctylterthiophene as ? bridge and 3-ethylrhodanine as electron-withdrawing end group. Side-chain engineering on BDT core exhibits small but measurable effect on the optoelectronic properties of small molecules. Theoretical simulation and X-ray diffraction study reveal the subtle tuning of interchain distance between conjugated backbones has large effect on the charge transport and thus the photovoltaic performance of these molecules. Bulk-heterojunction solar cells fabricated with a configuration of ITO/PEDOT:PSS/SM:PC71BM/PFN/Al exhibit a highest power conversion efficiency (PCE) of 6.99% after solvent vapor annealing.

| S-EPMC4853745 | biostudies-literature

Dibenzo[b,g]indeno-[1',2':3,4]fluoreno[1,2-d]oxonine-5,11,16,21-tetra-one.

Project description:The asymmetric unit of the title compound, C34H16O5, contains two independent mol-ecules (A and B) with similar conformations. The two benzene rings attached to the nine-membered ring are inclined to one another at 63.62 (14)° in mol-ecule A and 68.23 (12)° in mol-ecule B. One intra-moleculer C-H⋯O hydrogen bond occurs in mol-ecule A and two are observed in mol-ecule B. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming a three-dimensional network structure with R(2)2(10) and R(2)2(24) ring motifs. Aromatic π-π stacking interactions [centroid-centroid distances = 3.7572 (19), 3.6996 (19) and 3.7043 (19) Å] are also observed. The unit cell contains a pair of voids of 37 (2) Å(3) about an inversion centre but the residual electron density (highest peak = 0.19 e Å(-3) and deepest hole = -0.20 e Å(-3)) in the difference Fourier map suggests that no solvent mol-ecule occupies this void.

| S-EPMC3588961 | biostudies-literature

3-Methyl-benzo[1,2-c:5,4-c']dichromen-6(8H)-one.

Project description:The title compound, C21H14O3, crystallizes with eight independent mol-ecules (A-H) in the asymmetric unit which are arranged in four groups of two mol-ecules each (AB, CD, EF and GH). In each mol-ecule, the pyran-2-one ring is planar (r.m.s. deviations vary from 0.001 to 0.017?Å), while the pyran ring has a screw-boat conformation. In the crystal, mol-ecules stack in two columns, along the [10-1] direction, composed of mol-ecules C, B, E and G, and D, A, F and H. Mol-ecules A and F are linked via C-H?O hydrogen bonds. In addition, there are a number of C-H?? contacts present involving all of the mol-ecules. These inter-actions result in the formation of a three-dimensional network.

| S-EPMC4158523 | biostudies-literature

4,4'-(Ethene-1,2-diyl)dipyridinium bis-[4-(2-carboxy-benzo-yl)benzoate].

Project description:In the crystal structure of the title compound, C(12)H(12)N(2) (2+)·2C(15)H(9)O(5) (-), the cation has site symmetry with the mid-point of C=C bond located on an inversion center. The two benzene rings of the anion are oriented at a dihedral angle 85.87 (6)°. In the crystal, inter-molecular O-H⋯O and N-H⋯O hydrogen bonds link the cations and anions into supra-molecular double chains, which are further connected into a three-dimensional network through inter-molecular C-H⋯O and π-π stacking between parallel pyridine rings [centroid-centroid distance = 3.4413 (12)Å] and between parallel benzene rings [centroid-centroid distance = 3.6116 (14)Å].

| S-EPMC2971962 | biostudies-literature

1,2-Bis[(3,6,9-trimethyl-3,12-ep-oxy-3,4,5,5a,6,7,8,8a,9,10,12,12a-dodeca-hydro-pyrano[4,3-j][1,2]benzodioxepin-4-yl)-oxy]ethane.

Project description:The title compound, C(32)H(50)O(10), prepared from a mixture of ?- and ?-dihydro-artemisinin, has two ?-arteether moieties linked via an -OCH(2)CH(2)O- bridge, so that the mol-ecule is symmetric about the bridge. Each asymmetric unit contains a ?-arteether moiety and an -OCH(2) group, which is only one-half of the mol-ecule. The endo-peroxide bridges of the parent compounds have been retained in each half of the diol-bridged dimer. The rings exhibit chair and twist-boat conformations.

| S-EPMC3295452 | biostudies-literature

Ethyl 2-(3,4-dimethyl-5,5-dioxo-1H,4H-benzo[e]pyrazolo-[4,3-c][1,2]thia-zin-1-yl)acetate.

Project description:In the title mol-ecule, C(15)H(17)N(3)O(4)S, the heterocyclic thia-zine ring adopts a twist-boat conformation, which differs from that in related compounds, with adjacent S and C atoms displaced by 0.981?(4) and 0.413?(5)?Å, respectively, on the same side of the mean plane formed by the remaining ring atoms. The mean plane of the benzene ring makes a dihedral angle of 23.43?(14)° with the mean plane of the pyrazole ring. In the crystal, mol-ecules are connected by weak C-H?O hydrogen bonds to form a three-dimensional network. The H atoms of the methyl group attached to the pyrazole ring were refined over six sites with equal occupancies.

| S-EPMC3470368 | biostudies-literature

Effect of the ?-conjugation length on the properties and photovoltaic performance of A-?-D-?-A type oligothiophenes with a 4,8-bis(thienyl)benzo[1,2-<i>b</i>:4,5-<i>b</i>']dithiophene core.

Project description:Benzo[1,2-b:4,5-b']dithiophene (BDT) is an excellent building block for constructing ?-conjugated molecules for the use in organic solar cells. In this paper, four 4,8-bis(5-alkyl-2-thienyl)benzo[1,2-b:4,5-b']dithiophene (TBDT)-containing A-?-D-?-A-type small molecules (COOP-nHT-TBDT, n = 1, 2, 3, 4), having 2-cyano-3-octyloxy-3-oxo-1-propenyl (COOP) as terminal group and regioregular oligo(3-hexylthiophene) (nHT) as the ?-conjugated bridge unit were synthesized. The optical and electrochemical properties of these compounds were systematically investigated. All these four compounds displayed broad absorption bands over 350-600 nm. The optical band gap becomes narrower (from 1.94 to 1.82 eV) and the HOMO energy levels increased (from -5.68 to -5.34 eV) with the increase of the length of the ?-conjugated bridge. Organic solar cells using the synthesized compounds as the electron donor and PC61BM as the electron acceptor were fabricated and tested. Results showed that compounds with longer oligothiophene ?-bridges have better power conversion efficiency and higher device stability. The device based on the quaterthiophene-bridged compound 4 gave a highest power conversion efficiency of 5.62% with a VOC of 0.93 V, JSC of 9.60 mA·cm-2, and a FF of 0.63.

| S-EPMC5082721 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

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