From supramolecular chemistry to the nucleosome: studies in biomolecular recognition

• Marcey L. Waters

Beilstein J. Org. Chem. 2016, 12, 1863–1869, doi:10.3762/bjoc.12.175

• Marcey L. Waters Department of Chemistry, CB 3290, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, USA 10.3762/bjoc.12.175 Abstract This review highlights the author’s indirect path to research at the interface of supramolecular chemistry and chemical biology. Keywords: α

• -helices; aromatic interactions; β-hairpin peptides; cation–π interactions; dynamic combinatorial chemistry; histone; molecular recognition in water; nucleosome; π–π-stacking; post-translational modification; supramolecular chemistry; Review Childhood influences When thinking about how to start writing

• significant impact on how I run my own group. A turn to bioorganic chemistry An interesting thing happened while I was in graduate school. I found myself reading papers in a relatively young field: supramolecular chemistry. This interest did not simply spring forth on its own, however; the seeds were planted

Synthesis and properties of fluorescent 4′-azulenyl-functionalized 2,2′:6′,2″-terpyridines

• Adrian E. Ion,
• Liliana Cristian,
• Mariana Voicescu,
• Masroor Bangesh,
• Augustin M. Madalan,
• Daniela Bala,
• Constantin Mihailciuc and
• Simona Nica

Beilstein J. Org. Chem. 2016, 12, 1812–1825, doi:10.3762/bjoc.12.171

• : azulene; fluorescence; metal binding; synthesis; terpyridine; Introduction 2,2′:6′,2″-Terpyridine derivatives are extensively used organic ligands in the field of supramolecular chemistry and materials science [1][2][3][4]. Besides the interesting supramolecular architectures, metal–terpyridine complexes

Amidofluorene-appended lower rim 1,3-diconjugate of calix[4]arene: synthesis, characterization and highly selective sensor for Cu²⁺

• Rahman Hosseinzadeh,
• Mohammad Nemati,
• Reza Zadmard and
• Maryam Mohadjerani

Beilstein J. Org. Chem. 2016, 12, 1749–1757, doi:10.3762/bjoc.12.163

• great attention in supramolecular chemistry [1][2][3][4]. Copper is one of the crucial biological elements, which presents as catalytic cofactor for a variety of metallo-enzymes such as superoxide dismutase, cytochrome c oxidase, lysyl oxidase and tyrosinase, etc. [5][6][7][8][9]. However, excess

Organic chemistry meets polymers, nanoscience, therapeutics and diagnostics

• Vincent M. Rotello

Beilstein J. Org. Chem. 2016, 12, 1638–1646, doi:10.3762/bjoc.12.161

• supramolecular chemistry, along with a project in fullerenes [6][7]. After finishing my postdoctoral work, I moved to the University of Massachusetts. I chose UMass based on its quality and longstanding reputation for collaborative research. Upon arrival, I collected a fired up group of graduate students and

• cytosol (including materials destined to the nucleus), this entrapment is a major limitation [59]. One of the beauties of supramolecular chemistry is its modularity. We started looking into the use of the Pickering emulsions described above for delivery applications. There was a challenge: nobody

• (including us) could generate emulsions with diameters small enough (<200 nm) for use as in vivo delivery vehicles [60]. Once again, supramolecular chemistry came to the rescue. Anslyn showed that guanidinium groups bound strongly to carboxylates [61]. This led to the surmise that this interaction could be

Experimental and theoretical insights in the alkene–arene intramolecular π-stacking interaction

• Valeria Corne,
• Ariel M. Sarotti,
• Carmen Ramirez de Arellano,
• Rolando A. Spanevello and
• Alejandra G. Suárez

Beilstein J. Org. Chem. 2016, 12, 1616–1623, doi:10.3762/bjoc.12.158

• aromatic rings. This can be useful in several fields, such as supramolecular chemistry, biology and material science and, in particular, in the area of asymmetric synthesis for the rational design of new elements of stereocontrol. Intramolecular aryl–vinyl π-stacking interaction of a levoglucosenone

Dinuclear thiazolylidene copper complex as highly active catalyst for azid–alkyne cycloadditions

• Anne L. Schöffler,
• Ata Makarem,
• Frank Rominger and
• Bernd F. Straub

Beilstein J. Org. Chem. 2016, 12, 1566–1572, doi:10.3762/bjoc.12.151

• conditions [4][5][6]. The CuAAC reaction has found broad application in the preparation of peptide-conjugates [7][8], multicomponent syntheses [9], preparation of hydrogels, microgels and nanogels [10], (anion) supramolecular chemistry [11][12], in medicinal chemistry [13], therapeutics, biomaterials and

Synthesis of 2-substituted tetraphenylenes via transition-metal-catalyzed derivatization of tetraphenylene

• Shulei Pan,
• Hang Jiang,
• Yanghui Zhang,
• Yu Zhang and
• Dushen Chen

Beilstein J. Org. Chem. 2016, 12, 1302–1308, doi:10.3762/bjoc.12.122

• nonplanar distinct saddle-shaped structure [3][4], tetraphenylene and its derivatives have found broad applications in materials science [5][6][7][8][9][10][11], supramolecular chemistry [12][13][14][15][16][17][18], and asymmetric catalysis [19][20][21]. Since Rapson and co-workers reported the first

Synthesis of highly functionalized 2,2'-bipyridines by cyclocondensation of β-ketoenamides – scope and limitations

• Paul Hommes and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2016, 12, 1170–1177, doi:10.3762/bjoc.12.112

• catalysis, supramolecular chemistry or materials science and hence a large number of specifically substituted derivatives is known (for reviews and selected recent syntheses or applications see [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]). Due to the flexible and modular nature of our approach

Supramolecular chemistry at the interface of biology, materials and medicine

• Eric V. Anslyn and
• Steven C. Zimmerman

Beilstein J. Org. Chem. 2016, 12, 1101–1102, doi:10.3762/bjoc.12.105

• ; molecular recognition; molecular sensors; What do art, auto-mechanics, a rural Australian and Chinese village, two civil wars, and house building have to do with supramolecular chemistry? Unless you are an avid cover-to-cover reader of the Thematic Series of the Beilstein Journal of Organic Chemistry and

• happened upon the issue entitled “Supramolecular chemistry at the interface of biology, materials and medicine”, there is no possible way you would see the connection between these disparate items. In fact, these are part of the childhood recollections of several leading practitioners in the field of

• supramolecular chemistry and the authors of the mini-reviews in this Thematic Series. Before explaining the purpose of these recollections in more detail, an overview of this Thematic Series is needed. We had two main goals in putting this Thematic Series together: (1) to highlight where the field of

From steroids to aqueous supramolecular chemistry: an autobiographical career review

• Bruce C. Gibb

Beilstein J. Org. Chem. 2016, 12, 684–701, doi:10.3762/bjoc.12.69

• Bruce C. Gibb Department of Chemistry, Tulane University, New Orleans, LA 70118, USA 10.3762/bjoc.12.69 Abstract The focus of my group’s research is aqueous supramolecular chemistry; we try to understand how chemical entities interact with water and consequently how they interact with each other

• . This personal history recounts my career experiences that led to his involvement with this fascinating area of science. Keywords: supramolecular chemistry; Review I recall a conversation with J. Fraser Stoddart some years ago that now seems pertinent to this review. He asked a simple question, “what

• , but devilishly more complicated: water. More specifically, my research group is interested in the interactions between water and species dissolved in it. In short: aqueous supramolecular chemistry. We investigate supramolecular processes in water in order to identify new and interesting phenomenons

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

• Vito Rizzi,
• Sergio Matera,
• Paola Semeraro,
• Paola Fini and
• Pinalysa Cosma

Beilstein J. Org. Chem. 2016, 12, 549–563, doi:10.3762/bjoc.12.54

• appears to be 1:1 for all examined CDs. Keywords: cyclodextrins; inclusion complex; photodynamic therapy; Introduction Since several years, supramolecular chemistry has been considered the chemistry of the intermolecular bonds inducing the association of several chemical species with the formation of

• superstructures [1][2][3]. The Nobel laureate J. M. Lehn said that “supramolecular chemistry may be defined as chemistry beyond the molecule, bearing on the organized entities of higher complexity that result from the association of two or more chemical species held together by intermolecular forces. Its

Self and directed assembly: people and molecules

• Tony D. James

Beilstein J. Org. Chem. 2016, 12, 391–405, doi:10.3762/bjoc.12.42

• Tony D. James Department of Chemistry, University of Bath, Bath, BA2 7AY UK 10.3762/bjoc.12.42 Abstract Self-assembly and directed-assembly are two very important aspects of supramolecular chemistry. As a young postgraduate student working in Canada with Tom Fyles my introduction to

• Supramolecular Chemistry was through the self-assembly of phospholipid membranes to form vesicles for which we were developing unimolecular and self-assembling transporter molecules. The next stage of my development as a scientist was in Japan with Seiji Shinkai where in a “Eureka” moment, the boronic acid

Art, auto-mechanics, and supramolecular chemistry. A merging of hobbies and career

• Eric V. Anslyn

Beilstein J. Org. Chem. 2016, 12, 362–376, doi:10.3762/bjoc.12.40

• Eric V. Anslyn Department of Chemistry, University of Texas, Austin, TX 78712, USA 10.3762/bjoc.12.40 Abstract While the strict definition of supramolecular chemistry is “chemistry beyond the molecule”, meaning having a focus on non-covalent interactions, the field is primarily associated with

• draw for me to the fields of supramolecular chemistry and molecular orbital theory, because I grew up in a household filled with art. In addition to art, my childhood was filled with repairing and constructing mechanical entities, such as internal combustion motors, where many components work together

• to achieve a function. Analogously, the field of supramolecular chemistry creates systems of high complexity that achieve functions or perform tasks. Therefore, in retrospect a career in supramolecular chemistry appears to be simply an extension of childhood hobbies involving art and auto-mechanics

My maize and blue brick road to physical organic chemistry in materials

• Anne J. McNeil

Beilstein J. Org. Chem. 2016, 12, 229–238, doi:10.3762/bjoc.12.24

• field of supramolecular chemistry, specifically, and organic materials, broadly. My research group’s efforts toward designing new sensors based on small molecule gelators are described. In particular, I highlight how our design strategy has evolved as we learn more about molecular gelators. This

• perspective concludes with some predictions about where molecular gels, as well as my personal and professional life, are headed. Keywords: molecular gel; organic chemistry; organic materials; self-assembly; supramolecular chemistry; Review One of my earliest memories involves pouring water down our

A journey in bioinspired supramolecular chemistry: from molecular tweezers to small molecules that target myotonic dystrophy

• Steven C. Zimmerman

Beilstein J. Org. Chem. 2016, 12, 125–138, doi:10.3762/bjoc.12.14

• Steven C. Zimmerman Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, United States 10.3762/bjoc.12.14 Abstract This review summarizes part of the author’s research in the area of supramolecular chemistry, beginning with his early life influences and

• therapeutic agents for myotonic dystrophy using a rational design approach that heavily relies on principles of supramolecular chemistry. How this work was influenced by that of others in the field and the evolution of each area of research is highlighted with selected examples. Keywords: catenanes

• from research and teaching, the department head job was interesting, challenging, and highly rewarding in seeing the department move forward, especially with the help of our loyal alumni. We entitled the thematic issue containing this contribution “Supramolecular chemistry at the interface of biology

Supramolecular polymer assembly in aqueous solution arising from cyclodextrin host–guest complexation

• Jie Wang,
• Zhiqiang Qiu,
• Yiming Wang,
• Li Li,
• Xuhong Guo,
• Duc-Truc Pham,
• Stephen F. Lincoln and
• Robert K. Prud’homme

Beilstein J. Org. Chem. 2016, 12, 50–72, doi:10.3762/bjoc.12.7

• [112][113][114]. Conclusion and Perspective In this brief review it is shown that there is a plethora of routes to supramolecular polymer networks in aqueous solution based on cyclodextrin host–guest complexation. Through variations in this supramolecular chemistry at the molecular level macroscopic

Bright molecules for sensing, computing and imaging: a tale of two once-troubled cities

• A. Prasanna de Silva

Beilstein J. Org. Chem. 2015, 11, 2774–2784, doi:10.3762/bjoc.11.298

• remember. I was fortunate to be introduced to an Irish traditional band 17 years ago and we have kept on playing since then. Epilogue Since supramolecular chemistry concerns molecule–molecule interactions, its principles can be adapted to miniaturize people–people interactions or people–object interactions

Learning from the unexpected in life and DNA self-assembly

• Jennifer M. Heemstra

Beilstein J. Org. Chem. 2015, 11, 2713–2720, doi:10.3762/bjoc.11.292

• science and began to pave the road to my future career in chemistry. At every step along this road, I benefited from fantastic mentors who shared with me their enthusiasm for life and learning. I also grew to recognize my love of supramolecular chemistry, and this has been the constant theme driving my

• interesting to experience research in a chemistry lab. I read through all of the faculty research descriptions, and while I was still years away from recognizing an underlying love of supramolecular chemistry, I was immediately drawn to the work of Prof. James Nowick, whose lab was focused on constructing and

• choosing a graduate program, I had learned the phrase “supramolecular chemistry” and recognized my excitement for the process of designing, building, and studying functional molecular architectures. In the process of researching graduate programs, I read a series of papers from the lab of Prof. Jeff Moore

Synthesis and photophysical characteristics of polyfluorene polyrotaxanes

• Aurica Farcas,
• Giulia Tregnago,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert and
• Franco Cacialli

Beilstein J. Org. Chem. 2015, 11, 2677–2688, doi:10.3762/bjoc.11.288

• Aurica Farcas Giulia Tregnago Ana-Maria Resmerita Pierre-Henri Aubert Franco Cacialli Supramolecular Chemistry Group, ‘‘Petru Poni’’ Institute of Macromolecular Chemistry, Grigore Ghica Voda Alley, 700487-Iasi, Romania London Centre for Nanotechnology and Department of Physics and Astronomy

Assembly of synthetic Aβ miniamyloids on polyol templates

• Sebastian Nils Fischer and
• Armin Geyer

Beilstein J. Org. Chem. 2015, 11, 2646–2653, doi:10.3762/bjoc.11.284

• the supramolecular chemistry of Aβ with the concepts of reversible covalent chemistry. The present study shows how oligomers of the Hot=Tap dipeptide serve as templates for the reversible covalent esterification of boronic acids which mediate the assembly of monodisperse Aβ miniamyloids. The modular

Inclusion complexes of 2-methoxyestradiol with dimethylated and permethylated β-cyclodextrins: models for cyclodextrin–steroid interaction

• Mino R. Caira,
• Susan A. Bourne,
• Halima Samsodien and
• Vincent J. Smith

Beilstein J. Org. Chem. 2015, 11, 2616–2630, doi:10.3762/bjoc.11.281

• Mino R. Caira Susan A. Bourne Halima Samsodien Vincent J. Smith Centre for Supramolecular Chemistry Research (CSCR), Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa 10.3762/bjoc.11.281 Abstract The interaction between the potent anticancer agent 2-methoxyestradiol

• File 430: Additional data. Acknowledgements Members of the Centre for Supramolecular Chemistry Research who were involved in the study reported here express their thanks to the National Research Foundation (Pretoria) and the University of Cape Town for research support. Any opinion, findings and

Synthesis of bi- and bis-1,2,3-triazoles by copper-catalyzed Huisgen cycloaddition: A family of valuable products by click chemistry

• Zhan-Jiang Zheng,
• Ding Wang,
• Zheng Xu and
• Li-Wen Xu

Beilstein J. Org. Chem. 2015, 11, 2557–2576, doi:10.3762/bjoc.11.276

• addition, the application of bitriazoles and the related CuAAAC reaction in different fields, including medicinal chemistry, coordination chemistry, biochemistry, and supramolecular chemistry, have been highlighted. Keywords: bistriazoles; click chemistry; cycloaddition; homogeneous catalysis; oxidative

• dialkyne spacers In the past years, bistriazoles with dialkyne spacers have gained significant attention for their potential application in supramolecular chemistry, pharmaceutical chemistry, biological chemistry and organometallic chemistry. The construction of bistriazoles from dialkynes is now well

Smart molecules for imaging, sensing and health (SMITH)

• Bradley D. Smith

Beilstein J. Org. Chem. 2015, 11, 2540–2548, doi:10.3762/bjoc.11.274

• Bradley D. Smith University of Notre Dame, Notre Dame, IN 46530, USA 10.3762/bjoc.11.274 Abstract This autobiographical review provides a personal account of the author’s academic journey in supramolecular chemistry, including brief summaries of research efforts in membrane transport, molecular

• imaging, ion-pair receptors, rotaxane synthesis, squaraine rotaxanes, and synthtavidin technology. The article concludes with a short perspective of likely future directions in biomedical supramolecular chemistry. Keywords: fluorescence; ion-pair receptors; membrane transport; molecular imaging; rotaxane

• considered supramolecular chemistry. So it was a little risky to start an independent academic career in a field with no previous experience. Indeed my new lab had to start from the beginning and learn all the rudimentary supramolecular experimental techniques such as measuring binding constants and

Size-controlled and redox-responsive supramolecular nanoparticles

• Raquel Mejia-Ariza,
• Gavin A. Kronig and
• Jurriaan Huskens

Beilstein J. Org. Chem. 2015, 11, 2388–2399, doi:10.3762/bjoc.11.260

• core of the SNPs. Keywords: host–guest interactions; nanoparticles; self-assembly; stimulus-responsive; supramolecular chemistry; Introduction Self-assembly and molecular recognition are two core concepts underlying supramolecular chemistry. These offer convenient and versatile pathways to

Conformational equilibrium in supramolecular chemistry: Dibutyltriuret case

• Karina Mroczyńska,
• Małgorzata Kaczorowska,
• Erkki Kolehmainen,
• Ireneusz Grubecki,
• Marek Pietrzak and
• Borys Ośmiałowski

Beilstein J. Org. Chem. 2015, 11, 2105–2116, doi:10.3762/bjoc.11.227

• ; hydrogen bonding; NMR; rotamerism; supramolecular chemistry; Introduction The hydrogen bond (HB) is one of the most common non-covalent interactions. Since it stabilizes, for example, the double helix of DNA and influences peptide folding it is quite reasonable to assume that HBing is crucial for

• observations are in line with computations that are very useful in drawing conclusions. The use of benzoates with regularly changed properties may be the method of choice in analysis of complexes. The pre-organization of molecules used in supramolecular chemistry is, in general, important to this field. On the