Synthesis by the Hummelen-Wudl Method and Physicochemical Study of Pyropheophorbide-Fullerene Dyad

Alexei V. Kozlov,^a Alexander Yu. Rybkin,^a@ Alexandra Yu. Belik,^a Kamil R. Taziev,^b,a Pavel A. Tarakanov,^a,c Nikolay S. Goryachev,^a,b Ilya V. Sulimenkov,^d Viatcheslav I. Kozlovskiy,^d,c Yulia V. Romanenko,^e Mikhail O. Koifman,^e Fedor E. Gostev,^f Ivan V. Shelaev,^f Arsenii V. Aybush,^f Viktor A. Nadtochenko,^f and Alexander I. Kotelnikov^a,b

^aInstitute of Problems of Chemical Physics RAS, 142432 Chernogolovka, Russia

^bLomonosov Moscow State University, 119991 Moscow, Russia

^cInstitute of Physiologically Active Compounds RAS, 142432 Chernogolovka, Russia

^dChernogolovka Branch of the N.N. Semenov Federal Research Center for Chemical Physics, RAS, 142432 Chernogolovka, Russia

^eIvanovo State University of Chemistry and Technology, 153000 Ivanovo, Russia

^fN.N. Semenov Federal Research Center for Chemical Physics, RAS, 119991 Moscow, Russia

^@Corresponding author E-mail: alryb@icp.ac.ru

DOI: 10.6060/mhc200500r

Macroheterocycles 2020 13(2) 147-155

A new type of pyropheophorbide-fullerene[60] dyad was synthesized by their attachment by the cyclopropane backbone at the 13(1)-position of the chlorin macrocycle using the Hummelen-Wudl method. Here we report a complex analysis of the structure influence on the photophysical properties of the newly obtained dyad and its comparison with another pyropheophorbide-fullerene[60] dyad. The latter dyad was previously obtained by the attachment of the tetrahydropyrrole backbone at the third position of the macrocycle using the Prato reaction. It was shown by quantum-chemical modeling that the studied dyads have drastically different spatial positions of the fullerene core relative to the dye macrocycle plane: “parallel” for the former and “perpendicular” – for the latter. The influence of structural differences on various properties of dyads was studied: the aggregation properties, absorption spectra, the fluorescence quenching of the dye moiety in the dyads, and the lifetimes of excited states. The data obtained are important for the further development of methods for the directional design of the photoactive fullerene-dye structures – highly effective photosensitizers for photodynamic therapy.

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Synthesis by the Hummelen-Wudl Method and Physicochemical Study of Pyropheophorbide-Fullerene Dyad

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