Synthesis and photophysical properties of phosphorus(v) porphyrins functionalized with axial carbazolylvinylnaphthalimides

Abstract

We have synthesized new D-A-D type phosphorus(V) porphyrin derivatives and functionalized with axial carbazolylvinylnaphthalimide units. The absorption bands of the obtained phosphorus(V) porphyrins were in the range 250-640 nm with high molar absorption coefficients, meaning strong light-harvesting abilities. Notably, it is found that the devices based on phosphorus(V) porphyrins with a configuration structure of [ITO/PEDOT : PSS/organic active film/LiF/Al] give an incident-photon-to-current conversion efficiency (IPCE) response. The maximal IPCE value reaches 2.76% for the device based on compound , which is much higher than that of 0.20% for compound . The reason might be due to the low oxidation potential and the strong light-harvesting ability of the enlarged conjugation of the axial units in compound . Therefore, we deduced that photo-induced electron transfer happened in phosphorus(V) porphyrins bearing axial conjugated donor units, which would make them good candidates for photovoltaic materials that could be applied in solar cells.

Ultrafast charge separation and charge stabilization in axially linked ‘tetrathiafulvalene–aluminum(iii) porphyrin–gold(iii) porphyrin’ reaction center mimics

“…[19][20][21][22][23][24][25] This is mainly because of the synthetic challenges where two ligands cannot be attached using transition metal porphyrins. This problem can be addressed by using main group element porphyrins, such as aluminum(III) porphyrin, [26][27][28][29] tin(IV) porphyrin 27,[30][31][32][33][34][35][36] or phosphorus(V) porphyrins, 27,30,[37][38][39][40] which generally have one or two axial bonds and they can be utilized to attach redox active electron donor (D) and/or acceptor (A) units.…”

Linear Oligocarbazole‐Based Organogelators: Synthesis and Fluorescent Probing of Explosives

“…The synthetic routes to C3 and C5 are shown in Scheme . First, compounds 1 – 3 were prepared according to the procedures previously reported by our group 22,31–34. The target molecules of C3 and C5 were prepared by Heck reactions of compound 2 with compounds 1 and 3 , respectively, catalyzed by Pd(OAc) 2 in yields of 55 and 48 %.…”

“…Synthesis of C1, C3, and C5: 9‐ n ‐Hexadecylcarbazole ( C1 ), 9‐hexadecyl‐3‐vinyl‐9 H ‐carbazole ( 1 ), 9‐hexadecyl‐3,6‐diiodo‐9 H ‐carbazole ( 2 ), and ( E )‐9‐hexadecyl‐3‐[2‐(9‐hexadecyl‐9 H ‐carbazol‐3‐yl)vinyl]‐6‐vinyl‐9 H ‐carbazole ( 3 ) were prepared according to methods reported previously 9,20,31–34…”

Branched benzothiadiazole-cored oligomers with terminal carbazoles: Synthesis and fluorescence probing nitroaromatics

“…Compound 9-octyl-3-vinyl-9H-carbazole (3) [14], 4-(bis(4-iodophenyl)amino)benzaldehyde [15], 6-iodo-9-octyl-9H-carbazole-3-carbaldehyde [14], 4-(bis(4-((E)-2-(9-octyl-9H-carbazol-6-yl)vinyl)phenyl)amino)benzaldehyde (6) [16] and 4,7-dibromobenzo [c][1,2,5]thiadiazole [17] were synthesized according to the reported procedures. The Heck reaction between compound 3 and 4-bromobenzaldehyde catalyzed by Pd(OAc) 2 at 110 C for 24 h afforded compound 4 in a yield of 65%, which was transformed into compound 5 through Wittig reaction with methyltriphenylphosphoniumiodine in a yield of 83%.…”