NAIST Division of Materials Science

Patrick Calupitan of Photonic Molecular Science lab receives national French C’Nano award

Dr. Jan Patrick Calupitan of the Photonic Molecular Science Laboratory received the national French C’Nano award for Interdisciplinary Research during the C’Nano conference on December 12, 2018 in Toulon France for his PhD thesis on “Highly sensitive terarylenes: Synthesis, switching, and scanning tunneling microscopy studies”, in which he described his inspiring work spanning photochemistry, organic synthesis, calculations, and microscopy studies on photo- and electro-functional organic molecules.

【Dr. Jan Patrick Calupitan (left in the picture)】

C’Nano is the national network of French scientists and researchers recognized by the National Center for Scientific Research (CNRS) working on nanoscience and nanotechnology. They recognize two awardees among PhD students who graduated from French universities in three categories every year (fundamental, interdisciplinary and applied research).

Dr. Calupitan entered the Double Degree Program between NAIST and Paul Sabatier University in Toulouse, France, after he graduated from Ateneo de Manila University, Phillippins. First student enroll in this program, he received his PhD in 2018 from both universities. His PhD achievements has been also recognized as “NAIST Outstanding Student Award” in March 2018.

Photonic Molecular Science

Highly sensitive terarylenes: Synthesis, switching, and scanning tunneling microscopy studies

Jan Patrick Dela Cruz Calupitan

I would like to thank Prof. Kawai and Prof. Rapenne in NAIST and UPS for their mentorship and guidance all throughout my PhD studies. I also appreciate Assoc. Prof. Nakashima, Dr. Olivier Galangau, and my labo-mates in Photonic Molecular Science (NAIST) and CEMES (Toulouse) for their contributions.

Photoswitching diarylethenes have been sought for the next generation electronic devices because of their thermal bi-stability, high fatigue resistance, and rapid reaction. Modification of their central moiety to an aryl group, to generate terarylenes, led to previously unmet sensitivity to switching stimuli. Further, to make them viable for miniaturized electronic devices, it is necessary to study these class of molecules at the single molecular level by scanning tunneling microscopy (STM). This study has three parts: (1) highly-sensitive terarylenes; (2) their modification for STM studies; and (3) STM results. In the first part, it is shown that switching reactions maybe achieved efficiently. By a careful design of the molecules, the cycloreversion speed was 1000-times faster and 100-times more efficient. Terarylenes were functionalized with tert-butyl and chloro-groups. These modifications were shown to preserve the photochemical properties of the molecules while at the same time improving STM contrasts. Lastly, STM studies were performed. Initial experiments resulted in a novel method to create 2D nanoassemblies of terarylenes. Meanwhile, single molecular imaging revealed different surface conformers of the terarylene on the surface and mapping of molecular orbitals. This showed that multidisciplinary understanding of the chemical and physical aspects of molecules is necessary to advance them as building blocks for future technologies.

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