Abstract
donor–acceptorDonor–acceptor–π–acceptor–donor (D1-A1-π-A2/A3-D2)-type small molecules, such TPA-MC-2 and TPA-MC-3, were designed and synthesized starting from donor-substituted alkynes (TPA-MC-1) via [2 + 2] cycloaddition−retroelectrocyclization reaction with tetracyanoethylene (TCNE) and 7,7,8,8-tetracyanoquinodimethane (TCNQ) units, respectively. TPA-MC-2 and TPA-MC-3 chromophores differ on the A2/A3 acceptor subunit, which is 1,1,4,4-tetracyanobutadiene (TCBD) and a dicyanoquinodicyanomethane (DCQDCM), respectively. Both the derivative bearing same donors D1 (triphenylamine) and D2 (trimethylindolinm) and also same A1 (monocyano) as an acceptor, tetracyano with an aryl rings as the π-bridging moiety. The incorporation of TCNE and TCNQ as strong electron withdrawing units led to strong intramolecular charge-transfer (ICT) interactions, resulting in lower LUMO energy levels. Comparative UV–Vis absorption, fluorescence emission, and electrochemical and computational studies were performed to understand the effects of the TCNE and TCNQ subunits incorporated on TPA-MC-2 and TPA-MC-3, respectively.
Highlights
The fabrication of low-cost electronic devices such as bulk heterojunction (BHJ) and organic solar cells (OSCs) has become important in commercial applications because of their light-absorbing characteristics
The band gap engineering of such chromophores aims to improve the efficiency of the devices through the manipulation of highest occupied molecular orbitals (HOMO) and lowest unoccupied molecular orbitals (LUMO), has attracted wide attention of researchers [1,2]
We designed and synthesized small molecule conjugates D1-A1-π-A2/A3-D2 composed of electron donor and acceptor moieties
Summary
The fabrication of low-cost electronic devices such as bulk heterojunction (BHJ) and organic solar cells (OSCs) has become important in commercial applications because of their light-absorbing characteristics. The optoelectronic properties of chromophore could be altered by varying the strength of donor (D) or acceptor (A) subunits [4,5,6,7,8,9,10]. To achieve this researcher employed the cross-conjugation reaction to tune the LUMO energy level of chromophores [11,12,13,14,15].
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