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

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• 作者：Zhanqian Yu ; Marcin Ptaszek
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：November 1, 2013
• 年：2013
• 卷：78
• 期：21
• 页码：10678-10691
• 全文大小：589K
• 年卷期：v.78,no.21(November 1, 2013)
• ISSN：1520-6904

文摘

Design, synthesis, and optical properties of a series of novel chlorin鈥揵acteriochlorin energy transfer dyads are described. Each dyad is composed of a common red-absorbing (645鈥?46 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 (鈮?.77) even for chlorin鈥揵acteriochlorin 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 桅_f range of 0.155鈥?.23 in toluene and 0.12鈥?.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.