New derivatives of triphenylamine and naphthalimide as ambipolar organic semiconductors: Experimental and theoretical approach

New core-substituted with electron-donating group 1,8-naphthalimides towards optoelectronic applications

“…For a series of hydrazones with naphthalimides units, the first reduction potential was at -1.80 V, -1.84 V for compounds with alkyl substituted hydrazine linkages (reversible process) and -1.97 V, -1.99 V for NIs with unsubstituted hydrazine unit (irreversible process) [23]. These compounds undergo oxidation at the same potential at 0.09 V. For NIs with core-substituted directly with triphenylamine (TPA), estimated E red and E ox were laying between -1.80 V  -1.84V and -0.25  -0.57 V, respectively (reversible processes) [20]. Only slightly lower reduction onsets were measured for NIs contaning TPA connected with napthalene core by vinyl group (E red = -1.87 +/-10mV) [24].…”

“…The basic strategy for the synthesis of core-functionalized NIs usually starts from halogenated naphthalene dianhydride [12], [16], [20][21], [23][24]. In this work we explored the other possibility for core-modified NDI preparation based on utilization of naphthalene anhydride with nitro substituent at 3 core position.…”

“…Contrary to the electrochemistry of NDIs described in many papers [11 and literature cited therein] only a few reports, to the best of our knowledge, concern the electrochemical properties of core-modified 1,8-naphthalimides. The redox behavior of core-modified 1,8-naphthalimides was described by Guideika et al [20][21], [23][24]. For a series of hydrazones with naphthalimides units, the first reduction potential was at -1.80 V, -1.84 V for compounds with alkyl substituted hydrazine linkages (reversible process) and -1.97 V, -1.99 V for NIs with unsubstituted hydrazine unit (irreversible process) [23].…”

“…Various core-functionalized both NDIs and NIs have been reported and wide is the range of possible their applications [11][12], [14][15], [17][18][19][20][21][22][23][24]. NIs have been investigated as fluorescent sensors for metal ions [25], light emitting compounds [12], [16], [26], electron-transporting materials [21], ambipolar semiconductors [20], colorimetric chemosensor [27], solvatochromic fluorophores [28], lightharvesting antennae [29], active aniti-bacterical dyes [30] and anticancer applications [31].…”

Structural and optical characterizations of thin organic films of thioindigo

“…Ambipolar charge-transporting organic semiconductor materials are of great interest for many applications associated with organic light-emitting diodes [1]. Indigo is an intrinsically ambipolar organic semiconductor with the bandgap 1.7 eV, high and well-balanced electron and hole mobilities (~ 1×10 -2 cm 2 V -1 s −1 ), and a good stability with respect to degradation in air [2].…”