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David N. Reinhoudt

Publications and source records attributed to David N. Reinhoudt.

9 recordsLinked to original sources
PubMed2001

Noncovalent Synthesis Using Hydrogen Bonding.

Hydrogen bonds are like human beings in the sense that they exhibit typical grouplike behavior. As an individual they are feeble, easy to break, and sometimes hard to detect. However, when acting together they become much stronger and lean on each other. This phenomenon, which in scientific terms is called cooperativity, is based on the fact that "1+1 is more than 2". By using this principle, chemists have developed a wide variety of chemically stable structures that are based on the reversible formation of multiple hydrogen bonds. More than 20 years of fundamental studies on these phenomena have gradually developed into a new discipline within the field of organic synthesis, and is nowadays called "noncovalent synthesis". This review describes noncovalent synthesis based on the reversible formation of multiple hydrogen bonds. Starting with a thorough description of what the "hydrogen bond" really is, it guides the reader through a variety of bimolecular and higher order assemblies and exemplifies the general principles that determine their stability. Special focus is given to reversible capsules based on hydrogen-bonding interactions that exhibit interesting encapsulation phenomena. Furthermore, the role of hydrogen-bond formation in self-replicating processes is actively discussed, and finally the review briefly summarizes the development of novel materials (nanotubes, liquid crystals, polymers, etc.) and principles (dynamic libraries) that recently have emanated from this intriguing field of research.

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PubMed2001

Direct Observation of Surface-Controlled Self-Assembly of Coordination Cages by Using AFM as a Molecular Ruler We acknowledge the Nanolink Program of the MESA(+) Research Institute (University of Twente), the CNR Nanotechnology Programme, and MURST (Project Molecular Nanoelectronics) for financial support of this work. A special thanks goes to Dr. Maik Liebau (University of Twente) for the preparation of the microcontact-printed substrates and Dr. Frank Geurts (AKZO NOBEL, Central Research Arnhem, NL) for the XPS measurements.

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PubMed1998

Rhenium(V)-Salen Complexes: Configurational Control and Ligand Exchange.

Reactions of ReO(PPh(3))(2)Cl(3) with tetradentate bis(salicylideneamine) ligands, H(2)salpd (1) and H(2)salbd (2), in different alcohols gave the novel mixed-ligand rhenium complexes ReO(sal)OAlk (OAlk = variety of alkoxy ligands). Configurational studies show that the rhenium complexes ReO(salpd)OAlk (1a-f) display either a symmetrical or a nonsymmetrical configuration, depending on the size of the alcohol and its boiling point. The rhenium complexes ReO(salbd)OAlk (2a-d) are all nonsymmetrical due to the number of carbons that bridge the imine nitrogens. In the case of the symmetrical ReO(salpd)OMe (1a) complex the methoxy ligand can be exchanged for a number of ligands of different types (OAlk, OPh, SAlk, OC(O)Alk). In the newly formed complexes the original configuration was retained except for the ReO(salpd)SAlk (1i,j) complexes which were isolated in the nonsymmetrical configuration. Starting from the nonsymmetrical ReO(salpd)OPr (2c) complex, ligand exchange led to a mixture of the symmetrical and nonsymmetrical complexes, with ratios depending on the reaction time. The crystal structures of ReO(salbd)OPr (2c), and ReO(salpd)OPhOMe (1g) have been determined. ReO(salbd)OPr crystallizes in the triclinic space group P&onemacr;, Z = 2, with a = 10.0344(16) Å, b = 10.647(2) Å, c = 11.481(2) Å, alpha = 86.551(15) degrees, beta = 86.998(14) degrees, gamma = 80.112(15) degrees, V = 1205.1(4) Å(3), and final R = 0.0460. Crystals of ReO(salpd)OPhOMe are orthorhombic, space group P2(1)2(1)2(1), Z = 4, with a = 10.6222(15) Å, b = 12.442(3) Å, c = 16.354(3) Å, V = 2161.4(7) Å(3), and final R = 0.0371. Under the influence of traces of water a number of symmetrical complexes react to a "dimeric" structure, consisting of two ReO(salpd) moieties bridged by an oxygen atom with the bridging Re-O-Re angle symmetrically imposed at 180 degrees. [ReO(salpd)](2)O (3) crystallizes in the monoclinic, space group P2(1)/c, Z = 4, with a = 14.860(2) Å, b = 12.545(2) Å, c = 16.5111(17) Å, beta = 95.030(10) degrees, V = 3066.1(7) Å(3), and final R = 0.0439.

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PubMed1997

Novel Resorcinarene Cavitand-Based CMP(O) Cation Ligands: Synthesis and Extraction Properties.

Tetrafunctionalized resorcinarene cavitands (4-6) have been synthesized starting from tetrakis(bromomethyl)cavitand 3. New cavitand-based cation ligands with (carbamoylmethyl)phosphonate (CMP) and -phosphine oxide (CMPO) moieties (8a,b and 9a,b) were prepared via two different routes in good (45-86%) overall yields. The ligands (8a,b and 9b) are very effective europium extractants. Ph(2)CMPON(Pr)-cavitand 8b has the highest extraction constant, determined with radiotracer experiments, for 1:1 complexation with Eu(picrate)(3) (K(ex)(1) = 2.7 x 10(12) M(-)(4)). The steric preorganization of the four CMP(O) moieties on the resorcinarene cavitand improves the efficiency and selectivity [of Eu(III) over UO(2)(II) and Fe(III)] of the metal extraction processes, compared to simple CMP(O) extractants.

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PubMed1997

Water-Soluble Neutral Calix[4]arene-Lanthanide Complexes: Synthesis and Luminescence Properties.

Water-soluble calix[4]arenes 10a,b with chromophores ("antenna") attached to the lower rim via a short spacer are described. In the neutral lanthanide complexes of 10a,b photoexcitation of the antenna induces lanthanide emission via intramolecular energy transfer. Calix[4]arene 10b with a chrysene moiety as sensitizer shows strong lanthanide emission for Eu(3+) with an excitation maximum at lambda = 363 nm.

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PubMed1997

Head-to-Head Linked Double Calix[4]arenes: Convenient Synthesis and Complexation Properties.

Combination of calix[4]arenes functionalized at the upper rim at the 5- and 17-positions with amino and formyl groups, respectively, gives a new series of "head-to-head" linked double calix[4]arenes in nearly quantitative yield. The X-ray structure of a modified double calix[4]arene is reported. The novel, highly preorganized receptor molecules complex silver(I) ions (K(ass) = 9.5 x 10(5) M(-)(1) in CDCl(3)); the selectivity of complexation was studied by supported liquid membrane transport experiments and chemically modified field effect transistor measurements.

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PubMed1996

Lower Rim-Upper Rim Hydrogen-Bonded Adducts of Calix[4]arenes.

An upper-rim-substituted calix[4]arene tetracarboxylic acid forms hydrogen-bonded duplexes with lower-rim-substituted tetra(4-pyridyl)- and tetra(3-pyridyl)calix[4]arenes in chloroform. The formation of these adducts was studied by extraction experiments. The association constants determined via (1)H NMR dilution experiments in CDCl(3) are 7.6 x 10(3) and 1.3 x 10(3) M(-1) for the 4-pyridyl and the 3-pyridyl derivative, respectively. IR studies in the solid state and in solution indicate that the interaction is based on hydrogen bonding and that the degree of proton transfer is negligible. VPO measurements support the formation of 1:1 adducts.

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