Electrochemical and optical properties of substituted phthalimide based monomers and electrochemical polymerization of 3,4-ethylenedioxythiophene-polyhedral oligomeric silsesquioxane (POSS) analogue

Designing of DAD Type Small Semiconductor Molecules andInvestigation of Substituent Effect on Their Molecular, Electronic and Optical Properties: A DFT Study**

“…Aforecited recent report, 3,6-bis(thieno-2-yl)-N-propyl-phthalimide (T 2 P-Pr) and 3,6-bis((3,4-ethylenedioxy)thieno-2-yl)-Npropyl-phthalimide (E 2 P-Pr) were synthesized by Cihaner and Önal et al E onset ox = E onset red potentials were reported as 1.57 V/ À 1.28 V for T 2 P-Pr and as 1.25 V/À 1.36 V for E 2 P-Pr. [52] We calculated HOMO, LUMO and E gap energies for T 2 P-Pr and E 2 P-Pr from experimental E onset ox and E onset red potentials using empirical Bredas et al equations. [54,55] Then, a benchmark study was performed to determine the most reliable method for further calculations of designed small molecules.…”

“…Cihaner and Önal et al in 2019 synthesized thiophene and phthalimide based DAD type molecules and demonstrated their promising electrochemical and optical properties. [52] In a study by Köse in the in silico medium, it has been seen that some small molecules combined with thiophene-benzotriazolethiophene and thiophene-phthalimide-thiophene can be used as semiconductors for photovoltaics. [53] In accordance with the information mentioned above, obviously it can be seen that functional properties of organic semiconductors in photovoltaic and electrochemical biosensor applications are very important to get better performance and that reason was motivated us to design new small molecule semiconductors and investigate their molecular, electronic and optical properties.…”

“…To select the best computational approach, we performed a benchmark study on experimentally studied thiophene based 3,6-bis(thieno-2-yl)-Npropyl-phthalimide (T 2 PÀ Pr) and 3,6-bis((3,4-ethylenedioxy) thieno-2-yl)-N-propyl-phthalimide (E 2 PÀ Pr). [52] All studied molecules 1 a-10 a, 1 b-10 b, 1 c-10 c are gathered in Figure 1.…”

“…[19,20,28,23,[43][44][45] Small molecules with functional groups have also found applications in biosensors. [36,38,46,47] Thiophene, [1][2][3]8,18,[48][49][50][51][52][53] which has an important role for the adjusting HOMO/LUMO energies, is one of the most suitable donor units, and phthalimide, [19,[23][24][25]31,49,50,52,53] benzimidazole [14,51] and benzotriazole [6,[17][18][19][20]23,26,28,31,48,53] are the most widely used acceptors in the design of small molecule semiconductors. Cihaner and Önal et al in 2019 synthesized thiophene and phthalimide based DAD type molecules and demonstrated their promising electrochemical and optical properties.…”

Synthetic Routes to Silsesquioxane-Based Systems as Photoactive Materials and Their Precursors

“…Anchoring the POSS unit on 3,4-ethylenedioxythiophenes was explored by Önal and Cihaner et al [35,36,37]. They proposed an amidation reaction of amonipropyl(heptaisobutyl)POSS with anhydride, followed by a palladium-mediated Stille reaction to obtain the respective reagents, with moderate (44%–59%) yields.…”