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Ngy nay, trong cuc sng, chng ta lin tc s dng cc thit b in t, nh : in thoi thng minh, my tnh, my tnh bng, TV, K t khi tranzito (bng bn dn) u tin c gii thiu bi John Bardeen, William Shockley and Walter Brattain vo nm 1947, phn ln cc thit b c ch to da trn bn dn v c, c bit l silic. Tuy nhin, do hn ch v cng ngh lin quan n vic s dng silic, mt n lc ng k ang dnh cho vic pht trin cc thit b in t hu c. Cc c tnh ca cht bn dn hu c gip chng c kh nng ng dng rng ri trong nhiu lnh vc khc vi chi ph thp, linh hot cao. Bn dn hu c l thnh phn quan trng trong nhiu thit b in t nh th nhn dng, m vch in t, cc ma trn ch ng trong mn hnh (AMOLED), pin mt tri hay acquy. S xut hin ca cc thit b quang in hu c (OPV devices) v tranzito hu c hiu ng trng (OFET devices) gp phn quan trng trong vic thay i b mt th gii. Tranzito hu c hiu ng trng c ch to ch yu t 2 loi vt liu : cc polime lin hp hoc cc phn t lin hp nh. Cc OFET u tin c bo co trong nm 1968 da trn mt film in ha nn polithiophen. Bn nm sau, OFET da trn h lin hp vng thm ca phn t nh (h thiophen ngng t) c tm ra. Hiu nng ca cc OFET trong nhng nm qua c tng ln ng k v dn dn thay th cho s c mt ca cc bn dn silic. Thiophen v cc dn xut ca n c coi l chun mc cho mt OFET. Cc OPV hay cc thit b di ng u c s xut hin ca thiophen, di dng polime hay cc phn t nh. Tuy nhin, cc polithiophen i hi quy trnh cng ngh tng i phc tp, cc khuyt tt trong polime c th lm gim hiu sut ca thit b. Do , mt hng i tim nng hin nay tm ra cc phn t nh c kh nng ng dng cao. Mt trong s l h thiophen ngng t, tiu biu l thieno[3,2-b]thiophen v cc dn xut ca n. H thiophen ngng t l h d vng thm c s lin hp - (gia cc obitan khng lai ha trn C) v -p (gia cp electron t do trn S vi C C ) trn ton mch. trng thi c bn, cc electron chim y cc LUMO. Khi c nh sng kch thch, chng chuyn ln cc HOMO. i vi h thiophen ngng t, s chnh mc nng lng gia HOMO vi LUMO l nh, v chng tr thnh cc cht bn dn.

S chuyn dch electron ln mc nng lng cao hn to nn mt l trng. Do , hu ht cc h thiophen ngng t u thuc bn dn loi p. Mt s h thiophen ngng t tiu biu cho loi ny

 tng hp cc h d vng ngng t thiophen c th i theo nhng con ng khc nhau, phng php khc nhau nhng thng thng to ra h d vng ngng t ln thng xut pht t h d vng ngng t nh hn m c s l thiophen v thieno[3,2-b]thiophen. Trong bo co ny ti xin trnh by phng php in hnh tng hp nn 2 h d vng c s ny. Tng hp thiophen: Trong cng nghip tng hp thiophen t butan, buten, hay buta-1,3-ien cho tc dng vi lu hunh nhit khong 600oC.

Phn ng trn din ra theo c ch gc t do. C th thay lu hunh trong phn ng trn bng anhirit sunfur. Tng hp thieno[3,2-b]thiophen: T thiophen, bng phn ng brom ha tng hp dn xut 2,3,5-tribromthiophen. Kh ha chn lc dn xut tribromthiophen thu c 3-bromthiophen. Fomyl ha 3-bromthiophen bng N-fomylpiperiin c mt LDA trong THF, sau cho sn phm thu c tc dng vi etyl thioglycolat trong mi trng baz thu c etyl thieno[3,2-b]thiophen2-cacboxylat. Thy phn este thu c trong mi trng kim, sau axit ha thu c axit thieno[3,2-b]thiophen-2-cacboxylic v cacboxyl ha thu c thieno[3,2-b]thiophen. S tng hp nh sau:

Mt s phng php khc tng hp thieno[3,2-b]thiophen v dn xut theo cc s sau: Theo [D Prim, G. Kirsch, Synthesis of new 2-arylthieno[3,2-b]thiophenes, J. Chem. Soc. Perkintrano 1, 1994, p]. 2603. 3-bromthiophen c liti ha bng butylliti -78oC trong THF, sn phm thu c cho phn ng vi lu hunh, c liti thiophen-3-sunfua. Ankyl ha liti thiophen-3sunfua bng dn xut halogen trong THF, sau fomyl ha sn phm thu c bng DMF/POCl3 trong THF thu c 3-(ankylthio)-thiophen-2-cacbanehit. Cui cng thc hin ng vng nh EtONa trong EtOH. S ca qu trnh nh sau :

Theo [S. H. Jung, H. K. Kim, Palladium- catalyzed dired sylthesis, photophysical propertices and tunable electroluminescence of norvel silicon-base alternoting copolymer. Macromolecules 2000, 33, p9277]. i t 3,4-ibromthiophen, liti bng butylliti, sau lu hunh ha ri cho sn phm thu c tc dng vi ClCH2COOH, cui cng este ha vi MeOH thu c metyl 2-((4bromthiophen-3-yl)thio)axetat. Fomyl ha sn phm ny bng PhN(CHO)Me/POCl3 thu c metyl 2-((4-brom-2-fomyl-thiophen-3-yl)thio)axetat. Thc hin ng vng nh EtONa sau l Cu trong quinilin thu c 3-bromthieno[3,2-b]thiophen

Mt s hng chuyn ha ca thieno[3,2-b]thiophen v dn xut

Theo ti liu [D Prim, G. Kirsch, Synthesis of new 2-arylthieno[3,2-b]thiophenes, J. Chem. Soc. Perkintrano 1, 1994, p. 2603.] thieno[3,2-b]thiophen c chuyn ha qua hp cht c kim ri c chuyn ha thnh dn xut aryl.

Trong bo co ny, chng ti la chn con ng s (2) hay phn ng Suzuki. Phn ng Suzuki l phn ng ghp mch s dng hp cht c Bo c dng:

Phn ng Suzuki nh ni l phn ng quan trng em li nhiu ng dng trong cng nghip tng hp ha cht hin i. Cc cng trnh nghin cu cho thy paladi l loi xc tc hu hiu cho phn ng Suzuki. C ch phn ng Suzuki vi xc tc Paladi c trnh by nh sau:

Phn ng Suzuki tri qua 4 giai on : Giai on hot ha xc tc Giai on cng hp oxi ha Giai on trao i kim loi Giai on kh tch ti u ha phn ng Suzuki cn la chn cc iu kin Xc tc v ligand Xc tc thng s dng nht l Pd(PPh3)4, ngoi ra cn c xc tc khng c phi t nh l Pd(OAc)2 v PPh3. Dung mi v baz Baz

TlOH v TlOEt l baz c xem nh s b sung tng cng tc phn ng Suzuki. Ngoi ra s dng nhng baz mnh nh NaOH, Ba(OH)2 hay K3PO4 trong benzen v DME cng em li hiu qu cao v tc ghp i. Dung mi

Cc loi dung mi thng c s dng l DME (1,2-imetoxi etan), toluen, DMF (imetyl formamit), benzen, ioxan, THF (tetrahirofuran)