Synthesis of Highly Functionalized BOPHY Chromophores Displaying Large Stokes Shifts

Abstract

BOPHY dyes bearing bromo (in 5,5'-position) and iodo (in 4,4'-position) were synthesized. Double Knoevenagel reactions allow the extension of conjugation, resulting in an absorption above 625 nm. Selective cross-coupling reactions promoted by palladium(0) and microwave irradiation allow linking of a perylene module. These dyes are highly fluorescent, and the intramolecular cascade energy transfer from the perylene moiety to the BOPHY framework is almost quantitative, providing large virtual Stoke shifts (>5100 cm(-1)).

A fluorescent dye with large Stokes shift and high stability: synthesis and application to live cell imaging

“…To address this issue, great effects have been dedicated and a number of noted uorophore dyes with large Stokes shi (Dl $ 80 nm) have been developed. [24][25][26][27][28] However, some problems are encountered with them containing complicated structures, multi-steps reaction, and low yields.…”

Bio-Inspired Artificial Light-Harvesting Arrays Based on Boron(III)-Chelates

“…Ziessel et al have reported [13] on the properties of the first molecular dyad built around the BOPHY scaffold (Figure 8). Here, a perylene moiety has been linked to the BOPHY core by way of an ethynylene group, thereby ensuring both close proximity and strong π-conjugation.…”

Crystal structure of 2,7-diiodo-1,3,6,8-tetramethyl-bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine, C14H14B2F4I2N4

“…The first review paper on BOPHY was published in 2018 [10]. BODIPY is a typical member of FBC, which has received great interests owing to its excellent photo-stability and thermo-stability [11][12][13]. As far as we know, no halogenated BOPHY derivative has been reported.…”