Amphiphilic chlorins and bacteriochlorins in micellar environments. Molecular design, de novo synthesis, and photophysical properties

Aravindu, Kunche; Mass, Olga; Vairaprakash, Pothiappan; Springer, Joseph W.; Yang, Eunkyung; Niedzwiedzki, Dariusz M.; Kirmaier, Christine; Bocian, David F.; Holten, Dewey; Lindsey, Jonathan S.

doi:10.1039/c3sc51335a

Title: Amphiphilic chlorins and bacteriochlorins in micellar environments. Molecular design, de novo synthesis, and photophysical properties

Journal Article · Sat Jun 01 00:00:00 EDT 2013 · Chemical Science

DOI:https://doi.org/10.1039/c3sc51335a· OSTI ID:1086803

Aravindu, Kunche ^[1]; Mass, Olga ^[1]; Vairaprakash, Pothiappan ^[1]; Springer, Joseph W. ^[2]; Yang, Eunkyung ^[2]; Niedzwiedzki, Dariusz M. ^[2]; Kirmaier, Christine ^[2]; Bocian, David F. ^[3]; Holten, Dewey ^[2]; Lindsey, Jonathan S. ^[1]

North Carolina State University
Washington University in St. Louis
University of California-Riverside

The incorporation of amphiphilic tetrapyrrole macrocycles in organized media is of great value for a variety of fundamental photochemical studies, yet work to date has chiefly employed porphyrins rather than chlorins or bacteriochlorins. The latter absorb strongly in the red or near-infrared spectral region, respectively. Here, eight amphiphilic macrocycles (six chlorins and two bacteriochlorins) have been designed, synthesized and characterized; the compounds differ in long wavelength absorption (610–745 nm) and peripheral substituents (type of auxochrome, hydrophobic/hydrophilic groups). A methyl pyridinium or benzoic acid substituent at the 15-position provides a polar “tail” whereas a hydrophobic group distal thereto (in the chlorins) provides a lipophilic “head” for the spontaneous incorporation in organized media. The eight (bacterio)chlorins are characterized by static and time-resolved absorption and fluorescence spectroscopy in N,N-dimethylformamide (DMF) and three micellar environments (TX-100, CTAB, and SDS) as well as ultrafast transient absorption studies in DMF.

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Research Organization:: Washington Univ., St. Louis, MO (United States); Energy Frontier Research Centers (EFRC) (United States). Photosynthetic Antenna Research Center (PARC)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

DOE Contract Number:: SC0001035

OSTI ID:: 1086803

Report Number(s):: DE-SC0001035-80

Journal Information:: Chemical Science, Vol. 4, Issue 9; ISSN 2041-6520

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

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