Near-IR Emissive Chlorin-Bacteriochlorin Energy-Transfer Dyads with a Common Donor and Acceptors with Tunable Emission Wavelength

作者：Yu Zhanqian; Ptaszek Marcin^*

来源：Journal of Organic Chemistry, 2013, 78(21): 10678-10691.

DOI：10.1021/jo4016858

Design, synthesis, and optical properties of a series of of novel chlorin-bacteriochlorin energy transfer dyads are described. Each dyad is composed of a common red-absorbing (645-646 nm) chlorin, as an energy donor, and a different near-IR emitting bacteriochlorin, as an energy acceptor. Each bacteriochlorin acceptor is equipped with a different set of auxochromes, so that each of them emits at a different wavelength. Dyads exhibit an efficient energy transfer (%26gt;= 0.77) even for chlorin-bacteriochlorin pairs with large (up to 122 nm) separation between donor emission and acceptor absorption. Excitation of the chlorin donor results in relatively strong emission of the bacteriochlorin acceptor, with a quantum yield Phi(f) range of 0.155-0.23 in toluene and 0.12-0.185 in DMF. The narrow, tunable emission band of bacteriochlorins enables the selection of a series of three dyads with well-resolved emissions at 732, 760, and 788 nm, and common excitation at 645 nm. Selected dyads have been also converted into bioconjugatable N-succinamide ester derivatives. The optical properties of the described dyads make them promising candidates for development of a family of near-IR fluorophores for simultaneous imaging of multiple targets, where the whole set of fluorophores can be excited with the common wavelength, and fluorescence from each can be independently detected.

• 出版日期2013-11-1