First Triazole-Linked Porphyrin−Fullerene Dyads

Fazio, Michael A.; Lee, Olivia P.; Schuster, David I.

doi:10.1021/ol802889d

Cited by 7 publications

(3 citation statements)

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“…The preparation of B/TT tweezer required the preliminary synthesis of 5-(4-aminophenyl)-10,15,20-(3,5-tert-butylphenyl)porphyrin, B/T, 30 building block by reacting pyrrole with a binary mixture of 3,5-tert-butylphenylbenzaldehyde and 4-acetamidobenzaldehyde in the presence of BF 3 ÁEt 2 O catalyst. The desired mono-amidoporphyrin was recovered by preparative column chromatography and hydrolyzed in acidic conditions to produce the corresponding amino-derivative B/ T. Bis(porphyrin) receptor B/TT was prepared according to the ''one-flask'' synthetic protocol outlined in Scheme 1.…”

Section: Results and Discussion Synthesis And Characterization Of B/tmentioning

confidence: 99%

Bulky melamine‐based Zn‐porphyrin tweezer as a CD probe of molecular chirality

et al. 2011

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The transfer of chirality from a guest molecule to an achiral host is the subject of significant interest especially when, upon chiral induction, the chiroptical response of the host/guest complex can effectively report the absolute configuration (AC) of the guest. For more than a decade, dimeric metalloporphyrin hosts (tweezers) have been successfully applied as chirality probes for determination of the AC for a wide variety of chiral synthetic compounds and natural products. The objective of this study is to investigate the utility of a new class of melamine-bridged Zn-porphyrin tweezers as sensitive AC reporters. A combined approach based on an experimental CD analysis and a theoretical prediction of the prevailing interporphyrin helicity demonstrates that these tweezers display favorable properties for chiral recognition. Herein, we discuss the application of the melamine-bridged tweezer to the chiral recognition of a diverse set of chiral guests, such as 1,2-diamines, α-amino-esters and amides, secondary alcohols, and 1,2-amino-alcohols. The bulky periphery and the presence of a rigid porphyrin linkage lead, in some cases, to a more enhanced CD sensitivity than that reported earlier with other tweezers.

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Section: Results and Discussion Synthesis And Characterization Of B/tmentioning

confidence: 99%

Bulky melamine‐based Zn‐porphyrin tweezer as a CD probe of molecular chirality

et al. 2011

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“…On the other hand, por-phyrin triazoles were obtained by combining alkynyl prophyrins with 4-azido-and 3-azidobenzaldehyde by "click chemistry" under microwave irradiation conditions. [116] Scheme 58.…”

Section: Cycloadditions Of Azidesmentioning

confidence: 99%

Microwave‐Assisted 1,3‐Dipolar Cycloaddition: an Eco‐Friendly Approach to Five‐Membered Heterocycles

Piñeiro

Melo

2009

Eur J Org Chem

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The review describes the use of microwave technology to carry out 1,3-dipolar cycloaddition reactions, an important tool for the construction of five-membered heterocycles. Microwave methodology can be applied to generate 1,3-dipoles (nitrones, nitrile oxides, azomethine ylides, azomethine imines, nitrile imines, azides, carbonyl ylides) and to promote the subsequent cycloaddition and usually avoids harsh reaction conditions. This nonconventional energy source is able

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“…In the last several decades, the porphyrin chemistry has been explored to develop a series of novel macrocyclic compounds through peripheral functionalization of meso-tetraarylporphyrins. Recently, the copper (I)-catalyzed Huisgen 1,3-dipolar cycloaddition [14,15] of an azide with terminal alkyne has become a straightforward route to afford [1,2,3]-triazole as a chemical linker to connect porphyrins with various scaffolds such as fullerene [16][17][18], ferrocene [19] and carbohydrate [20] in a single molecular framework for the study of their photophysical and therapeutic properties. In addition, 1,2,3-triazole subunit is also found useful in the synthesis of meso-meso-linked porphyrin dimers [21] and carbon nanotube functionalized porphyrin analogues [22].…”

Section: Introductionmentioning

confidence: 99%