Highly Efficient Energy Transfer in Subphthalocyanine−BODIPY Conjugates

Abstract

Two novel subphthalocyanines substituted axially with a BODIPY or distyryl BODIPY moiety have been synthesized. Both systems exhibit a highly efficient photoinduced energy transfer process, either from the excited BODIPY to the subphthalocyanine core (for the former) or from the excited subphthalocyanine to the distyryl BODIPY unit (for the latter).

4,4′-Difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) as components of novel light active materials

“…The energytransfer quantum yield for both processes was calculated to be 98%. 26 Through-space energy transfer has also been shown to occur between a BODIPYezinc porphyrinephenanthroline and an Nunsubstituted imidazole-H 2 eporphyrinephenanthroline system. The imidazole-appended porphyrin is tethered to the zinc-porphyrinephenanthroline unit by hydrogen bonding between the imidazole NH and two of the phenanthroline nitrogens, as well as a coordinative bond between the zinc(II) centre and the imidazole free nitrogen.…”

Oligo(p‐phenylene ethynylene)–BODIPY Derivatives: Synthesis, Energy Transfer, and Quantum‐Chemical Calculations

“…[2] In recent years, several BODIPY derivatives attached to energy donors such as polycyclic aryl hydrocarbons, [3] oligothiophenes, [4] subphthalocyanines, [5] and to energy acceptors such as porphyrins, [6] perylenediimides, [7] subphthalocyanine, [5,8] fullerenes [9] and BODIPYs [10] have been reported. However, to the best of our knowledge, there is no report about oligo(p-phenylene ethynylene)s (OPEs) as donor or acceptor subunit in the energy-transfer system.…”

Comparative electronic structures and UV–vis spectra of tribenzosubporphyrin, tribenzomonoazasubporphyrin, tribenzodiazasubporphyrin, and subphthalocyanine: Insight from DFT and TDDFT calculations

“…Subphthalocyanines have nonplanar, bowl-like structures along with a 14 -electron aromatic core with a trigonal-pyramidal boron atom as the central atom. They exhibit strong UV-vis absorption, intense fluorescence, and remarkable nonlinear optical properties and hence can be potentially applied as chromophores in molecular electronics [14][15][16][17][18], nonlinear optics materials [5,[10][11][12][13][19][20][21][22], photodynamic therapy [23,24], and light-harvesting [25][26][27][28][29]. In 2006, the analogues of subphthalocyanines in which all meso-nitrogen atoms were substituted with the sp 2 -hybrid carbons, the tribenzosubporphyrines [30], were synthesized and characterized as their boron complexes.…”