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

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. Lastly, 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:
 [1];  [1];  [1];  [1];  [1];  [1];  [2];  [2];  [2];  [2];  [1]
  1. North Carolina State Univ., Raleigh, NC (United States). Dept. of Chemistry
  2. Univ. of Maryland Baltimore County (UMBC), Baltimore, MD (United States). Dept. of Chemistry and Biochemistry
Publication Date:
Research Org.:
North Carolina State Univ., Raleigh, NC (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1345217
Grant/Contract Number:  
FG02-96ER14632
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Porphyrins and Phthalocyanines
Additional Journal Information:
Journal Volume: 19; Journal Issue: 04; Journal ID: ISSN 1088-4246
Publisher:
World Scientific
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; auxochrome; artificial photosynthesis; chlorophyll; hydroporphyrin; hydrophilic; photomedicine

Citation Formats

Ra, Doyoung, Gauger, Kelly A., Muthukumaran, Kannan, Balasubramanian, Thiagarajan, Chandrashaker, Vanampally, Taniguchi, Masahiko, Yu, Zhanqian, Talley, Daniel C., Ehudin, Melanie, Ptaszek, Marcin, and Lindsey, Jonathan S. Progress towards synthetic chlorins with graded polarity, conjugatable substituents, and wavelength tunability. United States: N. p., 2015. Web. doi:10.1142/s1088424615500042.
Ra, Doyoung, Gauger, Kelly A., Muthukumaran, Kannan, Balasubramanian, Thiagarajan, Chandrashaker, Vanampally, Taniguchi, Masahiko, Yu, Zhanqian, Talley, Daniel C., Ehudin, Melanie, Ptaszek, Marcin, & Lindsey, Jonathan S. Progress towards synthetic chlorins with graded polarity, conjugatable substituents, and wavelength tunability. United States. doi:10.1142/s1088424615500042.
Ra, Doyoung, Gauger, Kelly A., Muthukumaran, Kannan, Balasubramanian, Thiagarajan, Chandrashaker, Vanampally, Taniguchi, Masahiko, Yu, Zhanqian, Talley, Daniel C., Ehudin, Melanie, Ptaszek, Marcin, and Lindsey, Jonathan S. Wed . "Progress towards synthetic chlorins with graded polarity, conjugatable substituents, and wavelength tunability". United States. doi:10.1142/s1088424615500042. https://www.osti.gov/servlets/purl/1345217.
@article{osti_1345217,
title = {Progress towards synthetic chlorins with graded polarity, conjugatable substituents, and wavelength tunability},
author = {Ra, Doyoung and Gauger, Kelly A. and Muthukumaran, Kannan and Balasubramanian, Thiagarajan and Chandrashaker, Vanampally and Taniguchi, Masahiko and Yu, Zhanqian and Talley, Daniel C. and Ehudin, Melanie and Ptaszek, Marcin and Lindsey, Jonathan S.},
abstractNote = {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. Lastly, 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.},
doi = {10.1142/s1088424615500042},
journal = {Journal of Porphyrins and Phthalocyanines},
number = 04,
volume = 19,
place = {United States},
year = {2015},
month = {4}
}

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