An Insight into Derivatization of closo-Dodecaborate and Synthesis and Application of Indocyanine Green Dye

  • The content of this Ph.D. thesis is divided into two main topics. The first chapter presents a novel synthesis of dodecahydro-closo-dodecaborate anion [B12H12]2- derivatives. Nowadays, boron-rich dodecahydro-closo-dodecaborate anion [B12H12]2- has gained wide interest and providing great opportunities in designing of various geometric and electronic structures with promising properties useful for modern host-guest chemistry and organoelement chemistry, in addition to its wide application in medicinal chemistry. Herein, we report our efforts on the development of a novel synthesis of cyclic oxonium derivatives of [B12H12]2-and effective approach to mono-halogenation [B12H11X]2- (X= I, Br, Cl) of dodecahydro-closo dodecaborate anion, the procedure yields therefore much purer material than any of the literature procedures, the yields are very high, and work-up is very straight-forward. Additionally, an attractive methodology for construction of B-N bond has been established. In general, derivatization of the dodecahydro-closo-dodecaborate dianion [B12H12]2- suffers from the lack of efficient methodology for introducing N-containing organic moieties to boron cage, thus, we have developed an approach based on the palladium-catalyzed cross-coupling amination of [B12H11I]2- . The new methodology provides broad scope of B12-N-containing organic moieties in good to excellent yield. The second chapter highlights the synthesis and application of heptamethine cyanine green dyes. In details, synthesis of heptamethine indocyanine green dyes by addressing different positions in the chemical structure of the cyanine dye skeleton with the aim to generate green dye with optimal aqueous solubility and fewer tendencies to form aggregation. The staining ability of dye, toxicity, and stability in aqueous solution have been investigated. Two of the new substances stained the model for inner limiting membrane (ILM) in green and showed good stability in aqueous solution.

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Publishing Institution:IRC-Library, Information Resource Center der Jacobs University Bremen
Granting Institution:Jacobs Univ.
Author:mahmoud aljoumhawy
Referee:Detlef Gabel , Gerd-Volker Röschenthaler, Maik Finze
Advisor:Detlef Gabel
Persistent Identifier (URN):urn:nbn:de:gbv:579-opus-1009822
Document Type:PhD Thesis
Date of Successful Oral Defense:2021/05/26
Date of First Publication:2021/06/08
Academic Department:Life Sciences & Chemistry
PhD Degree:Chemistry
Focus Area:Health
Call No:2021/5

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