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Progress towards synthetic chlorins with graded polarity, conjugatable substituents, and wavelength tunability

Doyoung Ra

Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA

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Kelly A. Gauger

Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA

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Kannan Muthukumaran

Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA

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Thiagarajan Balasubramanian

Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA

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Vanampally Chandrashaker

Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA

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Masahiko Taniguchi

Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA

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Zhanqian Yu

Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland 21250, USA

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Daniel C. Talley

Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland 21250, USA

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Melanie Ehudin

Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland 21250, USA

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Marcin Ptaszek

Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland 21250, USA

Corresponding author.

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, and

Jonathan S. Lindsey

Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA

Corresponding author, fax: +1 919-513-2830.

SPP full member in good standing.

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https://doi.org/10.1142/S1088424615500042Cited by:8 (Source: Crossref)

Abstract

Advances in chlorin synthetic chemistry now enable the de novo preparation of diverse chlorin-containing molecular architectures. Five distinct molecular designs have been explored here, including hydrophobic bioconjugatable (oxo)chlorins; a hydrophilic bioconjugatable chlorin; a trans-ethynyl/iodochlorin building block; a set of chlorins bearing electron-rich (methoxy, dimethylamino, methylthio) groups at the 3-position; and a set of ten 3,13-disubstituted chlorins chiefly bearing groups with extended π-moieties. Altogether 23 new chlorins (17 targets, 6 intermediates) have been prepared. The challenge associated with molecular designs that encompass the combination of "hydrophilic, bioconjugatable and wavelength-tunable" chiefly resides in the nature of the hydrophilic unit.

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