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Influence of distance in adamantane rigid spacer between electron donor and acceptor to photoinduced electron transfer and photodecarboxylation efficiency

Photodecarboxylation has been in the focus of intensive research because of potential applications in organic synthesis [1], as well as for the development of photocages [2]. Moreover, interest for photodecarboxylation has been initiated due to the fact that some nonsteroidal non-inflammatory drugs undergo photodecarboxylation, causing severe photoalergies [3]. Photodecarboxylation can also be initiated by phthalimide in a triplet excited state, which acts as a reducing agent in photoinduced electron transfer (PET) [4]. After turning our focus to photodecarboxylation of activated adamantyl γ-amino acid 1 [5], we have synthesized novel activated adamantyl α- (2), β- (3, 4), and δ-amino acids (5), and studied their photochemistry, with the aim to investigate the molecular structure influence to efficiency of PET between carboxylate as electron donor and phthalimide in the triplet excited state as electron acceptor. PET triggers photodecarboxylation that ultimately delivers different intramolecular or intermolecular radical-trapping products.

photoinduced electron transfer ; photodecarboxylation ; activated adamantyl amino acids

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