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View, the Methods Used to Prepare Both Heteroleptic and Heterometallic Metallomacrocycles Will Be Discussed in Detail © 2015 RAJARSHI SARKAR ALL RIGHTS RESERVED DESIGN AND SYNTHESIS OF HETEROLEPTIC AND HETEROMETALLIC METALLO-SUPRAMOLECULAR TERPYRIDINE ARCHITECTURES A Dissertation Presented to The Graduate Faculty of The University of Akron In Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy Rajarshi Sarkar December, 2Ńń5 i DESIGN AND SYNTHESIS OF HETEROLEPTIC AND HETEROMETALLIC METALLO-SUPRAMOLECULAR TERPYRIDINE ARCHITECTURES Rajarshi Sarkar Dissertation Approved: Accepted: _____________________________ _____________________________ Advisor Department Chair Dr. George R. Newkome Dr. Kim Calvo _____________________________ _____________________________ Committee Member Interim Dean of the College Dr. Wiley J. Youngs Dr. John Green _____________________________ _____________________________ Committee Member Dean of the Graduate School Dr. Christopher J. Ziegler Dr. Chand Midha _____________________________ _____________________________ Committee Member Date Dr. David A. Modarelli _____________________________ Committee Member Dr. Sadhan C. Jana ii ABSTRACT Inspiration from biological assemblies in Nature has produced an extraordinary amount of research in supramolecular chemistry. Various non-covalent interactions have been employed to design and synthesize numerous sophisticated architectures with unique structural and functional properties. Metallo-supramolecular constructs are primarily synthesized in a homoleptic assembly; whereas, a preprogrammed monomer is reacted with a suitable metal ion to produce the desired, highly symmetric architectures. On the other hand, structural variance in the supramolecular materials is instilled mainly by step-wise or dynamic assembly protocols. Owing to the unavailability of suitable building blocks and lack of control over the outcome of the assembly, study of these assembly methods has been limited. Two novel terpyridine-based bimetallic triangles were synthesized via a less explored supramolecular fusion approach. Syntheses of two homometallic cyclic trimer and two metallo-squares were achieved, and they were characterized by NMR and MS techniques. Mixing of triangular and the tetrameric units produced the desired bimetallic triangular complexes in quantitative yield. The multinuclear structures were characterized by 1H, 2D-COSY, 2D-NOESY, ESI- and TWIM-MS data. Tandem MS data provided information on the stability of these triangles. UV-vis and luminiscence data indicated metal-ligand charge transfer. iii Three bimetallic triangles were constructed by a step-wise directed assembly method. An oligomeric trimer was synthesized from a 60º-directed bisterpyridine ligand and was characterized by NMR and MS techniques. Three heterobimetallic triangular architectures were obtained by reacting the oligomeric trimer with Zn(II), Cd(II), and Fe(II). 1H, 2D-COSY, and 2D-NOESY NMR, ESI- and TWIM-MS data confirmed the proposed structures. Luminescence data showed the emission intensities of the triangles are lower than the linear trimer indicating quenching effect of Zn(II), Cd(II), and Fe(II) centers. Synthesis of a structural mimic of first-generation Sierpiski triangle was achieved via dynamic supramolecular assembly. The two required bis- and tetrakis-terpyridine ligands were synthesized and characterized. The ligands were reacted with Cd(II) in precise 1:1:3 molar ratio to obtain the desired complex in near quantitative yield. 1H, 2D-COSY, and 2D-NOESY NMR, ESI- TWIM-MS, and collision cross-section data confirmed the presence of a Sierpiski triangle as the sole product of the reaction. TEM provided the visualization of the desired architecture, shape, and size of the observed molecules, which fit perfectly the simulated parameters. iv DEDICATION I would like to dedicate this dissertation to my parents Manjusree and Sagar Sarkar, my elder brother Saptarshi Sarkar and my lovely wife Dripta. Without their unconditional love, support, and sacrifice I would not be here. "Research is to see what everybody else has seen, and to think what nobody else has thought" – Albert Szent-Gyorgyi "History may forget you, or misinterpret your accomplishments, or what you stood for. The ripples you leave behind may get redirected but the universe will never be able to forget the entropy you add. That’s the law. The Second Law of Thermodynamics." – Michael Stevens v ACKNOWLEDGMENTS I would like to express my gratitude to my advisor Prof. George R. Newkome, for all his ideas, advice and guidance. It was a pleasure and honor to work for him. I am also thankful to Dr. Charles N. Moorefield for all his help and advice over the years. Special thanks to all my present and past colleagues for their help and fruitful scientific discussions. I would also like to thank The University of Akron for providing me with all the wonderful facilities. I greatly appreciate my committee members Prof. Wiley J. Youngs, Prof. Christopher J. Ziegler, Prof. David A. Modarelli, and Prof. Sadhan C. Jana for their valuable input and for spending their precious time reading and revising my dissertation. vi TABLE OF CONTENTS Page LIST OF TABLES…………………………………………………………………..…...x LIST OF FIGURES……………………………………………………………………...xi LIST OF SCHEMES……………………………………………………………….…...xvi CHAPTER I. RECENT ADVANCEMENT IN HETEROLEPTIC AND HETEROMETALLIC SUPRAMOLECULAR ARCHITECTURES .......................................................... 1 1.1 Introduction ........................................................................................................ 1 1.2 Directed Step-wise Assembly Approach ........................................................... 3 1.2.1 Two-Dimensional Constructs .................................................................. 3 1.2.1.1 Molecular Triangles ..................................................................... 4 1.2.1.2 Molecular Squares ..................................................................... 10 1.2.1.3 Triangle-Square Equilibrium ..................................................... 18 1.2.1.4 Triangle-Square Non-equilibrium Mixtures .............................. 25 1.2.1.5 Triangles or Squares .................................................................. 26 1.2.1.6 Molecular Rectangles ................................................................ 27 1.2.1.7 Molecular Rhomboids ............................................................... 33 1.2.1.8 Higher Order Polygons .............................................................. 36 1.2.2 Three-Dimensional Constructs .............................................................. 39 1.2.2.1 Tetrahedrons .............................................................................. 40 1.2.2.2 Cube ........................................................................................... 44 vii 1.2.2.3 Octahedron ................................................................................. 46 1.2.2.4 Cuboctahedron ........................................................................... 47 1.2.2.5 Trigonal Bipyramids and Double Squares ................................. 49 1.2.2.6 Adamantoids .............................................................................. 52 1.2.2.7 Trigonal Prisms .......................................................................... 54 1.2.2.8 Tetragonal Prisms ...................................................................... 58 1.2.2.9 Molecular Boxes ........................................................................ 62 1.3 Dynamic Assembly Approach .......................................................................... 65 1.3.1 Tetra Coordinated System ..................................................................... 65 1.3.2 Penta Coordinated System ..................................................................... 68 1.3.3 Hexa Coordinated System ..................................................................... 71 1.4 Concluding Remarks ......................................................................................... 74 II. MULTICOMPONENT REASSEMBLY OF TERPYRIDINE-BASED MATERIALS: QUANTITATIVE METALLOMACROCYCLIC FUSION ........ 75 2.1 Introduction ...................................................................................................... 75 2.2 Results and Discussion .................................................................................... 76 2.3 Conclusion ....................................................................................................... 87 2.4 Experimental Section ....................................................................................... 88 III. STEP-WISE CONSTRUCTION OF BIMETALLIC TRIANGLES BY SITE SPECIFIC METALLATION ................................................................................. 93 3.1 Introduction ...................................................................................................... 93 3.2 Result and Discussion ...................................................................................... 94 3.3 Conclusion ..................................................................................................... 107 3.4 Experimental Section ..................................................................................... 108 viii IV. ONE-STEP, MULTICOMPONENT SELF-ASSEMBLY OF A FIRST- GENERATION SIERPISKI TRIANGLE: FROM FRACTAL DESIGN TO CHEMICAL REALITY ....................................................................................... 114 4.1 Introduction ...................................................................................................
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