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Methods to synthesize diverse collections of sub- stituted piperidines are valuable due to the prevalence of this heterocycle in pharmaceutical compounds. Here, we present a general strategy to access N-(hetero)arylpiperidines using a pyridine ring-opening and ring-closing approach via Zincke imine inter- mediates. This process generates pyridinium salts from a wide variety of substituted pyridines and (heteroaryl)anilines; hydro- genation reactions and nucleophilic additions then access the N- (hetero)arylpiperidine derivatives. We successfully applied high- throughput experimentation (HTE) using pharmaceutically relevant pyridines and (heteroaryl)anilines as inputs and developed a one-pot process using anilines as nucleophiles in the pyridinium salt-forming processes. This strategy is viable for generating piperidine libraries and applications such as the convergent coupling of complex fragments. 

Radical couplings of cyanopyridine radical anions represent a valuable technology for functionalizing pyridines, which are prevalent throughout pharmaceuticals, agrochemicals, and materials. Installing the cyano group, which facilitates the necessary radical anion formation and stabilization, is challenging and limits the use of this chemistry to simple cyanopyridines. We discovered that pyridylphosphonium salts, installed directly and regioselectively from C–H precursors, are useful alternatives to cyanopyridines in radical–radical coupling reactions, expanding the scope of this reaction manifold to complex pyridines. Methods for both alkylation and amination of pyridines mediated by photoredox catalysis are described. Additionally, we demonstrate late-stage functionalization of pharmaceuticals, highlighting an advantage of pyridylphosphonium salts over cyanopyridines. 

Abstract We present a resource for designing bistable developable mechanisms (BDMs) that reach their second stable positions while exterior or interior to a cylindrical surface. Analysis of the necessary conditions to create extramobile and intramobile cylindrical BDMs is conducted through a series of three tests. These tests contain elements of both existing and new mechanism design tools, including a novel graphical method for identifying stable positions of linkages using a single dominant torsional spring, called the principle of reflection. These tests are applied to all possible mechanism cases and configurations to identify why certain configurations will always, sometimes, or never be a BDM. Two tables summarize these results as a guide when designing extramobile and intramobile BDMs. The results are compared and demonstrated with a numerical simulation of 30,000+ mechanisms, including several example mechanisms that illustrate the concepts discussed in the work. Discussion is then provided on the implication of these results. 

Abstract Mechanisms that can both deploy and provide motions to perform desired tasks offer a multifunctional advantage over traditional mechanisms. Developable mechanisms (DMs) are devices capable of conforming to a predetermined developable surface and deploying from that surface to achieve specific motions. This paper builds on the previously identified behaviors of extramobility and intramobility by introducing the terminology of extramobile and intramobile motions, which define the motion of developable mechanisms while interior and exterior to a developable surface. The limits of motion are identified using defined conditions. It is shown that the more difficult of these conditions to kinematically predict may be treated as a non-factor during the design of cylindrical developable mechanisms given certain assumptions. The impact of toggle positions for each case is discussed. Physical prototypes demonstrate the results. 

Abstract In many origami-based applications, a device needs to be maintained in one or more fold states. The origami stability integration method (OSIM) presented in this paper provides an approach for graphically combining various techniques to achieve stability. Existing stability techniques are also categorized into four groups based on whether they are intrinsic or extrinsic to the origami pattern and whether they exhibit gradual or non-gradual energy storage behaviors. These categorizations can help designers select appropriate techniques for their application. The paper also contains design considerations and resources for achieving stability. Finally, two case studies are presented which use the OSIM and the technique categorization to conceptualize stability in origami-based devices. 

Abstract We demonstrate analytically that it is possible to construct a developable mechanism on a cone that has rigid motion. We solve for the paths of rigid motion and analyze the properties of this motion. In particular, we provide an analytical method for predicting the behavior of the mechanism with respect to the conical surface. Moreover, we observe that the conical developable mechanisms specified in this article have motion paths that necessarily contain bifurcation points, which lead to an unbounded array of motion paths in the parameterization plane. 

Abstract Mechanisms that can both deploy and perform desired tasks offer a multifunctional advantage over traditional mechanisms. Developable mechanisms (DMs) are devices capable of conforming to a predetermined developable surface and deploying from that surface to achieve specific motions. This paper presents new terminology that defines motion of developable mechanisms while interior and exterior to a developable surface. The limits of motion are identified using defined conditions, and it is shown that the more difficult of these conditions may be treated as a non-factor during the design of cylindrical developable mechanisms given certain assumptions. 

Abstract We demonstrate analytically that it is possible to construct a developable mechanism on a cone that has rigid motion. We solve for the paths of rigid motion and analyze the properties of this motion. In particular, we provide an analytical method for predicting the behavior of the mechanism with respect to the conical surface. Moreover, we observe that the conical developable mechanisms specified in this paper have motion paths that necessarily contain bifurcation points which lead to an unbounded array of motion paths in the parameterization plane.