5170-41-2Relevant academic research and scientific papers
Photochemical electron transfer in micellar systems and across surfactant vesicle bilayers promoted by esters of 2,1,3-benzothiadiazole-4,7-dicarboxylic acid
Grubb, Colin J.,Cole-Hamilton, David J.,Whittlesey, Michael K.
, p. 5005 - 5012 (1996)
The dibutyl (BTDB) and diethyl (BTDE) esters of 2,1,3-benzothiadiazole-4,7-dicarboxylic acid have been prepared (BTDB for the first time) and used in the transfer of electrons from morpholine ethene sulfonic acid (MESH) to 1,5-anthraquinone disulfonate (AQDS) in cetyltrimethylammonium bromide (CTAB) micelles, or across vesicle bilayers prepared from dioctadecyldimethylammonium bromide (DODAB). BTDB and BTDE act as light absorbers and then accept an electron directly from MES- before passing it to AQDS. Kinetic studies indicate that the rate determining step in micelles is the electron transfer from BTDB-. to AQDS, whilst in the vesicle system, at low concentration it is either the same step or diffusion of BTDB-. across the vesicle bilayer. At higher concentrations, the rate of electron transfer across the vesicle is independent of all [reagents] except H+, so we tentatively conclude that the rate determining step is charge compensating diffusion of H+ across the bilayer.
Direct Conversion of Benzothiadiazole to Benzimidazole: New Benzimidazole-Derived Metal–Organic Frameworks with Adjustable Honeycomb-Like Cavities
Zhao, Yingnan,Han, Xiao,Yu, Feihu,Wei, Donghui,Cheng, Qing,Meng, Xiangru,Ding, Jie,Hou, Hongwei
, p. 5246 - 5250 (2019/03/21)
Up to now, the direct conversion of the thiadiazole ring to other heterocyclic rings has been a very challenging task. Herein, a CdII-mediated alcohol-substitution strategy for direct conversion from benzothiadiazole to benzimidazole is reported. Experimental and molecular modeling studies on the role of the chelated metal ion in this in situ alcohol-substitution reaction revealed that it serves as an all-rounder that is involved in the insertion of alcohol, activation of the thiadiazole ring by coordinative interaction, and the sulfur-extrusion process. Interestingly, the insertion of alcohol occurs much earlier than the sulfur-extrusion process, supported by a water-mediated proton-transfer process. This strategy also is suitable for constructing new benzimidazole-derived MOFs [Cd2(HMBIDC2?)2]?4 H2O (Cd-BID-MOF-1, HMBIDC2?=2-methyl-1H-benzimidazole-4,7-dicarboxylate) and [Cd2(HPBIDC2?)2]?1/3 H2O (Cd-BID-MOF-2, HPBIDC2?=2-(3-hydroxypropyl)-2H-benzimidazole-4,7-dicarboxylate). Because the terminal hydroxyl group on the imidazole ring protrudes into the circular channel in rhombohedral Cd-BID-MOF-2, the cavity is closer to hydrophilic than the honeycomb-like cavity in Cd-BID-MOF-1 with similar 3D structure. This rare observation will provide a new strategy to develop in situ ligand-reaction synthesis of functional MOFs and useful chelation-assisted catalytic reactions in heteroaromatic chemistry.
Two 3D Cd(II) Metal-Organic Frameworks Linked by Benzothiadiazole Dicarboxylates: Fantastic S@Cd6 Cage, Benzothiadiazole Antidimmer, and Dual Emission
Cheng, Qing,Han, Xiao,Tong, Yue,Huang, Chao,Ding, Jie,Hou, Hongwei
supporting information, p. 1696 - 1705 (2017/02/15)
On the basis of the same benzothiadiazole (BTD) ligand 2,1,3-benzothiadiazole-4,7-dicarboxylic acid (H2L), two new isomers of three-dimensional (3D) BTD-derived Cd(II) metal-organic frameworks 1-2 {[S@Cd6L6]·xH2O}n were obtained by the different solvothermal reactions, which were structurally similar. Surprisingly, structural analyses reveal that in 1 or 2, one free sulfur atom was fixed in a Cd(II) cluster cage by strong intermolecular interaction to form the secondary building unit (SBU) S@Cd6. Each SBU S@Cd6 is connected by six L2- ligands and further extended into the 3D porous framework. In this work, the BTD antidimmer was evidenced by structural analysis and photophysical study. Furthermore, either 1 or 2 showed the uncommon dual emission, while only one emission was observed in the solution of ligand H2L. The dual-emission mechanism was also realized by the structural analysis and photophysical study. Interestingly, although there is slight difference in structure (regular octahedral cage in 1 and slightly distorted octahedral cage in 2), the changes in N2 adsorption capability and photophysical performance between 1 and 2 are obvious, where 2 shows smaller Brunauer-Emmett-Teller surface area, broader absorption of antidimmer, and longer dual-emission lifetimes. Interestingly, either 1 or 2, the dual emission was clearly red-shifted by increasing the solvent polarity or the acidity of ambience, respectively.
Unique structural micro-adjustments in a new benzothiadiazole-derived Zn(II) metal organic framework: Via simple photochemical decarboxylation
Han, Xiao,Cheng, Qing,Meng, Xiangru,Shao, Zhichao,Ma, Ke,Wei, Donghui,Ding, Jie,Hou, Hongwei
, p. 10314 - 10317 (2017/09/25)
The first example of micro-adjustments of a metal organic framework (MOF) structure was observed in a new Zn(ii) MOF (Zn-BTDC-M1) derived from a benzothiadiazole-4,7-dicarboxylic acid (H2BTDC) ligand using a light-driven decarboxylation process. Interestingly, such decarboxylation occurs at the non-chelated wing of the ligand, which induced a change in the capability of the MOF for physical N2 adsorption and chemical NH3 gas adsorption.
2,1,3-Benzothiadiazole-modified DNA
Garo, Florian,Haener, Robert
scheme or table, p. 2801 - 2808 (2012/07/13)
The use of 2,1,3-benzothiadiazole (BTD) as a structural element with advanced electronic properties for DNA hybrids is described. Bis(alkynyl)- and bis(carboxamide)-derived BTD units are shown to support duplex stability through interstrand stacking inter
