title: Molecular binding behaviors of pyromellitic and naphthalene diimide derivatives by tetrasulfonated 1,5-dinaphtho-(3n+8)-crown-n (n = 8, 10) in aqueous solution.
abstract: The highly affinitive and selective binding processes of tetrasulfonated 1,5-dinaphtho-38-crown-10 (1(4-)) and tetrasulfonated 1,5-dinaphtho-32-crown-8 (2(4-)) with pyromellitic diimide and naphthalene diimide derivatives bearing cationic terminal groups (PMDI(2+) and NDI(2+)) are comprehensively investigated in aqueous solution by (1)H NMR and UV/vis experiments, mass spectrometry, microcalorimetric titration, and crystallographic analysis. The binding process of host-guest complexation is thermodynamically driven by the large enthalpic gain and favorable entropic change with the high association constants in the range of 10(4)-10(6) M(-1) order of magnitude. Combined with our previously reported thermodynamic data of ethyl viologen (EV(2+)), it is found that the exclusively selective binding behaviors originate from the size/shape matching effect, as well as the electrostatic interaction between negatively charged hosts and positively charged guests and aromatic π-stacking interrelation between electron-rich donors and electron-deficient acceptors.
authors: Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
authors: Ling
authors: L
authors: Chen
authors: Ying-Ming
authors: YM
authors: Zhang
authors: Li-Hua
authors: LH
authors: Wang
authors: Yu
authors: Y
authors: Liu
mesh_terms: D001665:Binding Sites; D043844:Crown Ethers / Q000737:chemistry*; D018360:Crystallography, X-Ray; D055664:Electrochemical Techniques; D007094:Imides / Q000737:chemistry*; D007096:Imidoesters / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D012996:Solutions; D013056:Spectrophotometry, Ultraviolet; D013816:Thermodynamics; D014867:Water / Q000737:chemistry; D000097566:Cyclophanes
chemical_list: D043844:Crown Ethers; D007094:Imides; D007096:Imidoesters; D009281:Naphthalenes; D012996:Solutions; D014867:Water; C584180:1,5-dinaphtho-32-crown-8; C584179:1,5-dinaphtho-38-crown-10; C542131:naphthalenediimide; C045143:pyromellitic diimide; D000097566:Cyclophanes