Synthesis and Characterization of a Brønsted Pair Functionalized Shape-Persistent Macrocycle.

The first shape-persistent macrocycle 1 offering a Brønsted pair functionalized interior is described. Via postcyclization transformation, this heterosequenced compound can be obtained from its corresponding ester 2. The macrocycles differ dramatically in their characteristics such as solubility and appearance. Theoretical investigations suggest that those contrasts might originate from conformational changes due to the formation of a strong O-H-N hydrogen bond in 1.

[1]  W. Wang,et al.  Covalent organic frameworks. , 2012, Chemical Society reviews.

[2]  Yinghua Jin,et al.  Solution-phase dynamic assembly of permanently interlocked aryleneethynylene cages through alkyne metathesis. , 2015, Angewandte Chemie.

[3]  R. Krishna,et al.  Tailor-Made Pore Surface Engineering in Covalent Organic Frameworks: Systematic Functionalization for Performance Screening. , 2015, Journal of the American Chemical Society.

[4]  Qi Zhang,et al.  Terpene cyclization catalysed inside a self-assembled cavity. , 2015, Nature chemistry.

[5]  S. Wheeler,et al.  macrocycle embrace: encapsulation of fluoroarenes by m-phenylene ethynylene host. , 2015, Chemistry.

[6]  Linda S. Shimizu,et al.  Applications of a bis-urea phenylethynylene self-assembled nanoreactor for [2 + 2] photodimerizations. , 2014, The journal of physical chemistry. A.

[7]  Gang Zhang,et al.  Organic cage compounds--from shape-persistency to function. , 2014, Chemical Society reviews.

[8]  A. Navarro‐Vázquez,et al.  Preparation and characterization of a halogen-bonded shape-persistent chiral alleno-acetylenic inclusion complex. , 2014, Organic letters.

[9]  Iris M. Oppel,et al.  A permanent mesoporous organic cage with an exceptionally high surface area. , 2014, Angewandte Chemie.

[10]  Wei Zhang,et al.  Covalent assembly of heterosequenced macrocycles and molecular cages through orthogonal dynamic covalent chemistry (ODCC). , 2013, Organic letters.

[11]  Yinghua Jin,et al.  Highly efficient one-pot synthesis of hetero-sequenced shape-persistent macrocycles through orthogonal dynamic covalent chemistry (ODCC). , 2013, Chemical communications.

[12]  Chenfeng Ke,et al.  A simple and accessible synthetic lectin for glucose recognition and sensing. , 2012, Nature chemistry.

[13]  Frank Neese,et al.  The ORCA program system , 2012 .

[14]  S. Saito,et al.  Preparation of shape-persistent macrocycles with a single pyridine unit by double cross-coupling reactions of aryl bromides and alkynes. , 2011, The Journal of organic chemistry.

[15]  M. Iyoda,et al.  Conjugated macrocycles: concepts and applications. , 2011, Angewandte Chemie.

[16]  S. Grimme,et al.  A thorough benchmark of density functional methods for general main group thermochemistry, kinetics, and noncovalent interactions. , 2011, Physical chemistry chemical physics : PCCP.

[17]  S. De Feyter,et al.  Large all-hydrocarbon spoked wheels of high symmetry: modular synthesis, photophysical properties, and surface assembly. , 2010, Journal of the American Chemical Society.

[18]  M. Surin,et al.  Two-dimensional oligo(phenylene-ethynylene-butadiynylene)s: all-covalent nanoscale spoked wheels. , 2009, Chemistry.

[19]  Jeffrey S. Moore,et al.  Programmed dynamic covalent assembly of unsymmetrical macrocycles. , 2007, Journal of the American Chemical Society.

[20]  Jeffrey S. Moore,et al.  Shape-persistent macrocycles: structures and synthetic approaches from arylene and ethynylene building blocks. , 2006, Angewandte Chemie.

[21]  S. Höger,et al.  Cationic shape-persistent macrocycles: the unexpected formation of a nano-size supramolecular dimer. , 2006, Journal of the American Chemical Society.

[22]  P. Samorí,et al.  Shape-persistant macrocycles with terpyridine units: synthesis, characterization, and structure in the crystal. , 2003, Journal of the American Chemical Society.

[23]  M. Möller,et al.  Synthesis, aggregation, and adsorption phenomena of shape-persistent macrocycles with extraannular polyalkyl substituents. , 2001, Journal of the American Chemical Society.

[24]  Kawabata,et al.  Synthesis and association behavior of butadiyne-bridged , 2000, Organic letters.

[25]  S. Höger,et al.  Template-Directed Synthesis of Shape-Persistent Macrocyclic Amphiphiles with Convergently Arranged Functionalities , 1999 .

[26]  Ashok S. Shetty,et al.  Aromatic π-Stacking in Solution as Revealed through the Aggregation of Phenylacetylene Macrocycles , 1996 .