Synthesis, structure and photochromic properties of hybrid molecules based on fullerene C₆₀ and spiropyrans

Abstract

The 1,3-dipolar cycloaddition of azomethine ylides to fullerene C60 was utilized to perform the synthesis of spiropyran-containing photochromic pyrrolidinofullerenes.

Photocontrolled organic field effect transistors based on the fullerene C60 and spiropyran hybrid molecule

“…1a). 13 Simultaneously, for strict and objective comparison of our results with published data, we have fabricated a multilayer transistor, in which the semiconductor (fullerene C 60 ) and the light-controlled compound (spiropyran SpOx) formed separate layers (Fig. 1b).…”

“…In view of the above and as a continuation of our research towards the preparation and studies of properties of hybrid molecules based on fullerenes and photochromic compounds aimed at the design of more efficient and promising organic electronic devices, [13][14][15][16][17][18] we have fabricated and investigated a photocontrolled OFET containing pyrrolidinofullerene 1 as the active layer ( Fig. 1a).…”

Synthesis, photo and acidochromic properties of spiropyran-containing methanofullerenes

“…In view of high sensitivity of initial spiropyrans to a broad range of external stimuli 10,23-30 and to pursue our research aimed at the development of efficient synthetic routes to new molecular switches based on fullerenes and photochromic compounds, [14][15][16][31][32][33] we investigated photochromic and acidochromic behaviors of methanofullerenes 2, 7-10, 18-24.…”

“…12 An important place is occupied by studies directed towards the development of nanomaterials with controlled properties, e.g., light controlled carbon nanomolecules, fullerenes, nanotubes and graphenes. [13][14][15] Recently, 16 we performed for the rst time the successful chemical bonding of C 60 fullerene to spiropyrans via the Prato reaction and found 17 that the photochromic properties of pyrrolidinofullerenes are substantially affected by the nature of the electron-withdrawing group in the pyran ring.…”

Photo-Transformation Trajectories of Nitro-Spiropyran in Hybrid Compounds with [60]Fullerene

“…The absorption by merocyanine forms are observed experimentally in nSP-PF 60 , whereas the hybrid compound substituted by Cl or F atoms do not display photochromism. 21,22 The low-lying n* states formed by the lone pairs of the nitro substituents was proposed to change the photochromic mechanism of the dissipative excited-state through the S  (nSP)  Figure 1. Structure and accepted standard numbering of nSP (a) and nMC (b) where green circle lines denote atoms which contribute the most to the difference between the ground S G,|0,0 and excited S ,|1,0 configurations.…”