Described here are the synthetic details en route to an array of 2-nm-tall anthropomorphic molecules in monomeric, dimeric, and polymeric form. These anthropomorphic figures are called, as a class, NanoPutians. Using tools of chemical synthesis, the ultimate in designed miniaturization can be attained while preparing the most widely recognized structures: those that resemble humans.

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New electron-deficient fluorinated oligo(phenylene ethynylenes) (OPEs) with varied functional groups were synthesized as free thiols, nitriles, and pyridines, ready to be used for surface adhesion. Calculated dipole moments suggest better matching between energy levels of bulk interfaces and molecular frontier orbitals when compared to nonfluorinated OPEs. Differential scanning calorimetry confirmed a higher thermal stability than the nonfluorinated counterparts. Surface analysis by ellipsometry, contact angle goniometry, cyclic voltammetry, and surface infrared and X-ray photoelectron spectroscopy verified that the OPEs chemisorb on Au and Pt surfaces. On the basis of the physical properties of the fluorinated OPEs, they might be useful in future physical vapor deposition techniques, methods that are typically used in standard semiconductor fabrication processes.

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The fragmentation chemistry of the protonated and ionized nanoPutian 1 has been studied in the gas phase via electrospray ionization and tandem mass spectrometry.A direct analogy was observed between the fragmentation chemistry of this fascinating "humanoid molecule" and "cleavages" at certain parts of the human body. We argue that such direct analogy and illustrative schemes for the fragmentation of molecular ions of 1 offer a ludic and efficient tool to teach and capture attention to ion chemistry in mass spectrometry. Using the changes in mass for the two heavier nanoPutians with different head styles but the same body design, the analogy has also been used to predict mass spectra. The concepts of isotopic labelling and dissociation thresholds have also been illustrated. For many years, the approach has been successfully used by one of us in classes and lectures, mainly when presenting ion chemistry to students and audiences from fields other than Chemistry, most particularly from Biology, Medicine, and Forensic Chemistry.

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