Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

Abstract

Phthalocyanines and subphthalocyanines are attracting attention as functional dyes that are applicable to organic solar cells, photodynamic therapy, organic electronic devices, and other applications. However, phthalocyanines are generally difficult to handle due to their strong ability to aggregate, so this property must be controlled for further applications of phthalocyanines. On the other hand, trifluoroethoxy-substituted phthalocyanines are known to suppress aggregation due to repulsion of the trifluoroethoxy group. Furthermore, the electronic characteristics of phthalocyanines are significantly changed by the strong electronegativity of fluorine. Therefore, it is expected that trifluoroethoxy-substituted phthalocyanines can be applied to new industrial fields. This review summarizes the synthesis and application of trifluoroethoxy-substituted phthalocyanine and subphthalocyanine derivatives.

Fluorous phthalocyanines and subphthalocyanines

“…Fluorous phthalocyanines and subphthalocyanines have attracted our interest as a result of their applications in organic field-effect transistors [16], organic light-emitting diodes [17], photovoltaics [18], nonlinear optical materials [19], and photodynamic therapy [20]. To date there are limited reports describing the properties of phthalocyanines and subphthalocyanines in the fluorous phase [21,22].…”

Enantioselective Benzylation and Allylation of α-Trifluoromethoxy Indanones under Phase-Transfer Catalysis

“…The role of fluorine in medicinal chemistry is expanding rapidly after it was discovered that the introduction of fluorine into an organic molecule could productively influence its physical and chemical properties [1,2,3,4,5,6,7,8,9,10,11,12,13,14]. In particular, the trifluoromethoxy (OCF 3 ) functional group has received extensive attention in recent years in the fields of pharmaceuticals and agrochemicals, owing to its unique three-dimensional electronic properties, suitable lipophilic properties, and good metabolic stability [15,16,17,18,19,20].…”

Enantioselective Benzylation and Allylation of α-Trifluoromethoxy Indanones under Phase-Transfer Catalysis

“…The role of fluorine in medicinal chemistry is expanding rapidly after it was discovered that the introduction of fluorine into an organic molecule can productively influence its physical and chemical properties. [1][2][3][4][5][6][7][8][9][10][11][12][13][14] In particular, the trifluoromethoxy (OCF3) functional group has received extensive attention in recent years in the fields of pharmaceuticals and agrochemicals, owing to its unique three-dimensional electronic properties, suitable lipophilic properties, and good metabolic stability. [15][16][17][18][19][20] In fact, the OCF3 group is present in more than 1393 biologically active organic compounds according to a check of the PubChem database in June 2019.…”