title: Progress Towards Synthetic Chlorins with Graded Polarity, Conjugatable Substituents, and Wavelength Tunability.
abstract: Advances in chlorin synthetic chemistry now enable thede novopreparation of diverse chlorin-containing molecular architectures. Five distinct molecular designs have been explored here, including hydrophobic bioconjugatable (oxo)chlorins; a hydrophilic bioconjugatable chlorin; atrans-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.
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA.
authors.forename: Doyoung
authors.initials: D
authors.lastname: Ra
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA.
authors.forename: Kelly A
authors.initials: KA
authors.lastname: Gauger
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA.
authors.forename: Kannan
authors.initials: K
authors.lastname: Muthukumaran
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA.
authors.forename: Thiagarajan
authors.initials: T
authors.lastname: Balasubramanian
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA.
authors.forename: Vanampally
authors.initials: V
authors.lastname: Chandrashaker
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA.
authors.forename: Masahiko
authors.initials: M
authors.lastname: Taniguchi
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland 21250.
authors.forename: Zhanqian
authors.initials: Z
authors.lastname: Yu
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland 21250.
authors.forename: Daniel C
authors.initials: DC
authors.lastname: Talley
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland 21250.
authors.forename: Melanie
authors.initials: M
authors.lastname: Ehudin
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland 21250.
authors.forename: Marcin
authors.initials: M
authors.lastname: Ptaszek
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA.
authors.forename: Jonathan S
authors.initials: JS
authors.lastname: Lindsey
keywords: artificial photosynthesis; auxochrome; chlorophyll; hydrophilic; hydroporphyrin; photomedicine