Synthesis and spectral properties of new 3,3’-bis(dipyrrolylmethene) with acetylene spacer

Asymmetric Dipyrrin and F-BODIPYs Conjugated to Terminal Alkynes and Alkenes

“…not isolated at the pre-ligand step. 29,30,41,[51][52][53][54][55] Burgess reported the synthesis of an asymmetric F-BODIPY similar to 4 and bearing a terminal alkyne at the β-position of the dipyrrinato core, but the constituent dipyrrin was not isolated. 55 We first synthesized the asymmetric dipyrrin hydrobromide salt 9, bearing a TMSprotected alkynyl unit (Scheme 1).…”

“…The b-iodo pyrrole 7 55 underwent Sonogashira cross-coupling reaction conditions with TMS-acetylene to afford pyrrole 8. 51 Condensation of 8 and the α-free pyrrole 3 afforded the TMS-protected dipyrrin hydrobromide salt 9. However, upon treatment of 9 with NEt 3 and BF 3 •OEt 2 , loss of the TMS-group was accompanied by decomposition rather than formation of the corresponding F-BODIPY.…”

Structural diversity in the solid-state architectures of bis(4-pyridyl)acetylene and its derivatives

“…Spacers are essential components of the structural makeup of chemical compounds [1][2][3][4][5] and one spacer group that has drawn considerable attention to itself is the monomeric acetylene spacer. This is in connection to its wide range of applications in areas that are chemistry-related [6][7][8]. A striking peculiarity of acetylene bridge(s) as inclusion units in polymers, oligomers, dendrimers and related compounds is their capability to impose linearly conformed shapes on their hosts, thus enhancing their abilities to complex with metal ions, combine with other organic ligands or with self in the solid state.…”

“…A striking peculiarity of acetylene bridge(s) as inclusion units in polymers, oligomers, dendrimers and related compounds is their capability to impose linearly conformed shapes on their hosts, thus enhancing their abilities to complex with metal ions, combine with other organic ligands or with self in the solid state. The linearity of the acetylene linkages in turn conforms on their hosts an all-round rigidity as well as noncollapsible cavities [6][7][8][9][10][11]. Other than the fact that the introduction of an acetylene spacer is an effective method to mitigate steric strain between two subunits such as the pyridyl [12] or phenyl derivatives [13], it has played prominent roles as a building block in generating quite a number of fascinating crystalline frameworks.…”

Synthesis and reactivity of 2-thionoester pyrroles: a route to 2-formyl pyrroles

“…Cognisant that a Knorr-type synthesis of 2-carboxylate pyrroles yields 30-60% of the desired product on the same scale, this synthetic approach to 2thionoester pyrroles is in keeping with the most prevalent of the routes to functionalised pyrroles. 37,38 The corresponding benzyl thionoester pyrrole was synthesised following a similar approach, but originating with the reaction of CS 2 with benzyl alcohol in the presence of potassium hydroxide to produce the required potassium O-benzyl carbonodithioate starting material.…”