title: Synthesis, structure, and properties of supramolecular charge-transfer complexes between bis(18-crown-6)stilbene and ammonioalkyl derivatives of 4,4'-bipyridine and 2,7-diazapyrene.
abstract: 4,4'-Bipyridine and 2,7-diazapyrene derivatives (A) having two ammonioalkyl N-substituents were synthesized. The complex formation of these compounds with bis(18-crown-6)stilbene (D) was studied by spectrophotometry, cyclic voltammetry, (1)H NMR spectroscopy, and X-ray diffraction analysis. In MeCN, π-donor D and π-acceptors A form supramolecular 1:1 (D·A) and 2:1 (D·A·D) charge-transfer complexes. The D·A complexes have a pseudocyclic structure as a result of ditopic binding of the ammonium groups to the crown-ether fragments. The better the geometric matching between the components, the higher the stability of the D·A complexes (log K up to 9.39). A key driving force of the D·A·D complex formation is the excessive steric strain in the precursor D·A complexes. The pseudocyclic D·A complexes involving the ammoniopropyl derivative of 4,4'-bipyridine were obtained as single crystals. Crystallization of the related ammonioethyl derivative was accompanied by transition of the D·A complexes to a structure of the (D·A)(m) coordination polymer type.
authors: Photochemistry Center, Russian Academy of Sciences, ul. Novatorov 7A-1, Moscow 119421, Russian Federation.
authors: Artem I
authors: AI
authors: Vedernikov
authors: Evgeny N
authors: EN
authors: Ushakov
authors: Asya A
authors: AA
authors: Efremova
authors: Lyudmila G
authors: LG
authors: Kuz'mina
authors: Anna A
authors: AA
authors: Moiseeva
authors: Natalia A
authors: NA
authors: Lobova
authors: Andrei V
authors: AV
authors: Churakov
authors: Yuri A
authors: YA
authors: Strelenko
authors: Michael V
authors: MV
authors: Alfimov
authors: Judith A K
authors: JA
authors: Howard
authors: Sergey P
authors: SP
authors: Gromov
mesh_terms: D003300:Copper / Q000737:chemistry*; D043844:Crown Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D003460:Crystallization; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry*; D011721:Pyrenes / Q000737:chemistry*; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C568374:2,7-diazapyrene; D043844:Crown Ethers; D009942:Organometallic Compounds; D011108:Polymers; D011721:Pyrenes; D011725:Pyridines; D013267:Stilbenes; C568375:bis(18-crown-6)stilbene; D003300:Copper; C034306:4,4'-bipyridyl