Syntheses of Thiophene-Thiophene-Linked Corrorin Dimers with Tunable Near-Infrared Absorption and Distinctive ReactivityShow others and affiliations
2024 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 26, no 2, p. 571-576Article in journal (Refereed) Published
Abstract [en]
Thiahexaphyrinone 1 and thia-dipyrrin-appended corrorin 2 have been synthesized. Surprisingly, further oxidation of compound 2 with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in dichloromethane afforded dimer 3 with two molecules of compound 2 linked at the alpha-carbon atoms of the thienyl units. Treatment of compound 3 with DDQ in MeOH and SnCl2 in tetrahydrofuran/H2O afforded the dimethoxy-attached dimer 4 and hydrogenated dihydroxy-attached dimer 5, respectively. These results provide the first examples for synthesizing thiophene-linked porphyrinoid dimers with tunable near-infrared absorption and chirality.
Place, publisher, year, edition, pages
AMER CHEMICAL SOC , 2024. Vol. 26, no 2, p. 571-576
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:liu:diva-200675DOI: 10.1021/acs.orglett.3c04323ISI: 001146456500001PubMedID: 38190656OAI: oai:DiVA.org:liu-200675DiVA, id: diva2:1835447
Note
Funding Agencies|National Natural Science Foundation of China; East China University of Science and Technology (ECUST) [22131005, 22201074, 22075077, 21971063]; National Natural Science Foundation of China [23QA1402100]; Shanghai Rising-Star Program [23ZR1415600, 22ZR1416100]; Natural Science Foundation of Shanghai [2018-05973, 2020-04600]; Swedish Research Council [JPMXS0320220200]; Ministry of Education, Culture, Sports, Science and Technology (MEXT) Leading Initiative for Excellent Young Researchers
2024-02-062024-02-062024-02-06