Abstract
Towards the development of potential new organic photovoltaic and optoelectronic materials, a simple route to synthesize flexibly ether linked fullerene-bis[oligo-(phenylene-alt-thiophene)] and evaluation of electrochemical, photophysical and magnetic properties is presented. Flexible ether linking of oligo-phenylene-thiophene chain to 1, 2 C60(OH)2 is achieved employing Williamson’s ether synthesis. 7-chain phenylene-thiophene chain fluorescent conducting oligomer is synthesized using Grignard coupling reaction with preservation of bromo end groups. Oligomer is highly ordered and soluble in all organic solvents while on linking to fullerene-diol, solubility of adduct restricts only to dimethyl sulfoxide (DMSO). All the synthesized materials are characterized through spectroscopic techniques and molecular weight is determined by mass spectrometry and GPC. Properties of the material indicate the substantial effect of fullerene. High quenching in fluorescence intensity and strong paramagnetic property are observed in this material.
Highlights
Several fullerene-based donor-acceptor dyads [1,2,3,4] synthesized so far through the attachment of polymeric or oligomeric chain to fullerene have resulted in improved photovoltaic efficiency [5,6]
Away from conventional methods resulting in rigid cyclo-additions [7,8], exohedral addition of hydroxyl groups on fullerene provides several sites for flexible attachment for other molecules [9,10,11,12,13,14,15,16,17,18]
Fullerenol is appeared to be very notorious owing to non-specified attachment of hydroxyl groups onto its surface but supposed to be the most applicable molecule due to its high reactivity, stability and solubility
Summary
Several fullerene-based donor-acceptor dyads [1,2,3,4] synthesized so far through the attachment of polymeric or oligomeric chain to fullerene have resulted in improved photovoltaic efficiency [5,6]. Present article describes a simple and convenient method for stepwise synthesis of regioregular bromo end capped 7-chain phenylene-alt-thiophene oligomer (5) and its further attachment to 1,2-fullerene-diol to achieve novel photovoltaic materials (6). One of the strong advantages of this synthesis route is that the use of both cryogenic temperatures and highly reactive metals is not required and this method offers quick and easy preparation of oligomer in large scale. These reactions are carried out either at room temperature or in reflux condition. Evaluation of thermal, photophysical and magnetic properties of the material indicates substantial effect of fullerene on the thermal behavior as well as high quenching in fluorescence intensity and strong paramagnetic property
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