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[ CAS No. 75464-52-7 ] {[proInfo.proName]}

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Chemical Structure| 75464-52-7
Chemical Structure| 75464-52-7
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Product Citations

Product Citations      Expand+

West, Sarah M ; Tran, Duyen K ; Kaminsky, Werner , et al. DOI:

Abstract: We report herein the synthesis, electronic structure, experimental and density functional theory (DFT) calculated optical properties, and electrical conductivity of a new π-conjugated ladder polymer, ladder poly(thienobenzothiazine) (LTBT), and its model compound, thienobis- (benzothiazine) (TBBT). The synthesis of LTBT in a mixed polyphosphoric acid/sulfolane solvent system gave an intrinsic viscosity of 2.0 dL/g at 30 °C in methanesulfonic acid, and the polymer could form large-area freestanding films. Single-crystal X-ray structure of TBBT showed that it crystallizes in an orthorhombic structure with a coplanar thienobenzothiazine ladder backbone, which is in agreement with the DFT calculated structure. The electrochemically derived HOMO and LUMO energy levels of ?5.17 eV and ?3.75 eV of LTBT thin films revealed the p-type semiconducting nature of the conjugated ladder polymer. We thus p-doped LTBT thin films with FeCl3, leading to an average electrical conductivity of 0.3 S/cm. These results demonstrate the potential of the new ladder polymer LTBT in organic electronics while providing valuable insights into the structure?property relationships of semiconducting ladder .

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Sarah M. West ; Duyen K. Tran ; Jiajie Guo , et al. DOI:

Abstract: In this work, we show how N-alkyl substitution affects the chain conformation, electronic structure, and optical and charge transport properties of π-conjugated ladder poly(pyrrolobenzothiazines)s (LPBTs). We found that the π-conjugated backbones of the LPBTs have a donor–acceptor motif, which enabled a small bandgap of 1.5 eV that is unchanged by N-alkyl substitution. We found that partial protonation of the LPBTs in acid solutions resulted in increased backbone flexibility evidenced by thermochromism in solution and planar/nonplanar chain conformational variation with degree of protonation that we saw in density functional theory (DFT) calculations. The average field-effect hole mobility increased from 1.3 × 10[–3] cm2/(V s) in LPBT-Me to 3.1 × 10[–3] cm2/(V s) in LPBT, which can be explained by the increased crystallinity and decreased lattice disorder in LPBT. The results of our investigations of the solution and solid-state properties of the two ladder poly(pyrrolobenzothiazine)s provide new insights into the structure–property relationships of π-conjugated ladder polymers.

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Product Details of [ 75464-52-7 ]

CAS No. :75464-52-7 MDL No. :MFCD00142835
Formula : C6H10Cl2N2S2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :HVXLKRWRWNFGBA-UHFFFAOYSA-N
M.W : 245.19 Pubchem ID :14618269
Synonyms :

Calculated chemistry of [ 75464-52-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 2.0
Molar Refractivity : 63.68
TPSA : 129.64 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.46
Log Po/w (WLOGP) : 3.05
Log Po/w (MLOGP) : 2.02
Log Po/w (SILICOS-IT) : 0.98
Consensus Log Po/w : 1.7

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.28
Solubility : 0.129 mg/ml ; 0.000525 mol/l
Class : Soluble
Log S (Ali) : -4.83
Solubility : 0.00366 mg/ml ; 0.0000149 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -1.9
Solubility : 3.12 mg/ml ; 0.0127 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.4

Safety of [ 75464-52-7 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405 UN#:2811
Hazard Statements:H301+H311+H331-H315-H319 Packing Group:Ⅲ
GHS Pictogram:
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